2 comments/ 24041 views/ 9 favorites The Blue Diamond Club Ch. 01 By: MiloDeLaJolla A Crossdresser's Misadventures Had I gone too far? My rectum was half full of warm soapy water and about to be topped off with hot jizz - from someone pretending to be my father. My skirt had ridden up to my waist, and my garter belt was barely still clinging to my now shredding nylon stockings as my hairless cock and balls flapped with each thrust of my new Papa's cock regularly sliding inside my asshole. I looked at my bright-red toenails peeking out of the black peep-toe pumps with my legs wrapped around his torso as I cried, "Please sir, cum inside me. I want it so fuckin' bad." He was breathing hard, but without letting go of my arms pinned over my head, Papa continued the rhythmic pumping and placed his lips on mine, inserting his tongue. It started only a few hours before on a dull Saturday afternoon. I was freshly dressed in fem attire. With my legs freshly shaved, I looked cute in the mirror with a formfitting hot pink silky blouse tucked into black leather mini skirt, seamed stockings and four-inch spike heel pumps. I'd done my makeup; blue eye shadow with that smoky look and bright-red lipstick. You look too hot to stay in again tonight; I thought. Maybe I should have thought twice, but I was ready for some nasty action. Turning to Craigslist, I spotted an ad that stood out: Older trim Bi Male...very clean age: 48 height: 5'8" Enjoy all forms of sensuality...anal stimulation...role play and fantasy... erotic enemas...safe fucking...groups CD's, TV's, M/F couples, gay & bi guys - all welcomed Send stats... pics... details of specific interests He was twenty years older. In my heels, I'd tower over him by five inches. I moved the cursor to close the tab. However, one thing was holding me back. My cock was rock hard inside my satiny panties. I felt a rush of excitement as my CD clitty strained against the fabric. My erect clit didn't always make the safest decisions, but it knew what it liked. I pulled up a couple picts from the hard drive. I've always liked the ones of me in a blue satin pencil skirt and matching platforms. They showed lots of my slender legs and curvy ass. I decided to add something to make him especially responsive; I dropped my panties and took a selfie of my throbbing clit and labeled it "Right now - thinking about you." In the email, I expressed my desire for a take charge type and inventiveness in role playing. Attaching the photos, I clicked send without remorse and waited for a reply. The wait wasn't long; ten minutes tops. The guy was into everything and up-front about it; a total prev. I liked that he could express his desires. It's such a turn off to deal with someone who can only reply to a sexual offer with a brief sentence that translates to nothing more than "Yeah, let's fuck." This guy had ideas and told about himself. The pictures included some nice nude face shots. He looked well build, his manhood stiff, and that he knew how to use it. We exchanged phone calls and an hour later I was on my way. My cock quivered with excitement, and precum wetted my panties on the drive. He'd told me to bring some extra outfits to model, which thrilled me. I carried the bag with me to his front door and rang. He'd mentioned on the phone that we'd start with an unspecified role-play game. I was to go with it, enjoy and there'd be a big surprise later. "Hi, I'm Paul, come on in," he said as the door opened. He wore only tee-shirt and shorts, and I could see was in great shape for his age, standing with an air of authority. I smiled with approval. "I'm Cassi." I walked in, my high heels clicking on the tile entry flooring, yet he remained in place rather than stepping back. He took my right hand. "Please to meet you Princess." He ran his eyes up and down my body, taking me all in while lingering the longest on my shapely legs. Paul had a devilish glint in his eyes; his smile told me he liked what he saw. "You are a hot little tramp, aren't you?" With that, he kissed me full on the lips. As the kiss lingered, I could feel his tongue dart in and out of my mouth. I felt his hand run up and down my ass. While still holding my hand, he led me into his living room. The furnishings said 'divorced'; a cloth couch and a leatherette easy chair dominated the room. Across the kitchen counter, he mixed us drinks as we made small talk. He insisted I sip a girly Cosmopolitan Cocktail through a thin straw that I let caress my cherry red lips. I noticed the protruding budge in his shorts. Since he wasn't wearing underwear, it was easy to glimpse his erection. "Impressed? To tell you the truth, Princess, I'm a member of the Blue Diamond Club," he said with a sly laugh. "I don't know what that is, baby." Again he laughed. "If you're a good girl, I may let you join. You'll see what it's all about shortly. In the meantime, you'll address me as 'Papa'. I'm going to be your daddy tonight. Ever fucked your daddy?" So this was going to be an incest fantasy. This was different from anything I'd done before. "No, sir, I've never let him fuck me. I've been a princess too long." I stooped to my knees. With a slight tug, I released his erect member through the leg of his shorts. The head was nicely cut, and I guessed it to be about seven inches long. I opened my mouth and slowly inserted it. I moved his cock back and forth across my lips lapping at the tip. "You've become quite a little cock sucker, haven't you? You've sucked lots of cocks, since I sent you to college. You're a dirty little skank now." With that, he pulled me up and in one, swift motion dragged me across his knee. He swatted my ass firmly and resoundingly. My leather mini was unceremoniously hiked over my hips, and my panties pulled down to my thighs. Papa then landed a sharp slap against my exposed buttocks. I breathed deeply, knowing another blow would be coming. He smacked my other cheek with even more force. The way I wriggled on his lap told him I approved. More slaps rained across my butt turning it warm and red. He led me to his sofa, and I sat across his legs. He ran his hands up and own my nylon encased thighs as we kissed passionately. My ass still shuddered from its spanking. His hand worked its way to my crotch and I felt a jolt of electricity as he caressed my shaft. "You have a nice little clitty, my dear." My penis is at best five inches when fully erect, which may be why I've always identified with being a 'gurl'. My head was spinning from the attention of my swollen clit and the strong booze. Papa pulled his hand up toward my face. His palm covered with my precum; he made me lick it clean. Soon afterward, we moved to his upstairs bedroom. Beside the bed hung an enema bag that bulged with fullness, and a tube set freshly lubed. "All for you, Princess. Get into position." He positioned me on the bed on my knees and ass in the air. Papa wiped my sphincter clean and inserted the tip and ran the tube what felt like a foot past my anal opening. He released the hose clip, and I felt warm water flowing into me. He had me lay flat and rimmed my asshole with his tongue for a fabulous five minutes. "Go to the bathroom and release most, but leave about a third. It'll increase the entire sensation for you." By the time I returned to the bedroom, he was still rock hard. Papa examined my swollen clit and began to gently stroke my erection. Slowly at first and gradually picking up the cadence. Mentally, I fought hard not to cum. I wanted to keep my horny buzz going while getting fucked. My precum was self-lubricating for Papa as he rubbed his hand over my cock and balls. For several minutes, I heard someone moaning. It took some time before I realized the moans were coming from me. With a few more skillful strokes, I released my pent-up load. I gushed in a warm white stream that left a thin soggy trail up my shirt and blouse and reaching as far as my throat. Without thinking, I screamed a torrent of verbal obscenities, like I was a teenaged virgin experiencing her first orgasm in the back seat of an SUV. "Oh shit, I didn't want to cum yet," said as I recovered my senses. Usually I preferred to ejaculate after I'd been fucked. "Don't worry about shooting your load, I can help you out, Princess. I want you to enjoy this nearly as much as I'm going to." With that, he reached onto his nightstand, grabbed something and placed it into my opened mouth. The pill was tiny, and I swallowed accidentally. I felt a sense of panic. I didn't do recreational drugs. Papa saw the look in my eyes and sought to reassure me. "No, it's not a drug. Well, not the kind that will get you high. I've just given you some Viagra. In about twenty minutes, you'll be harder than iron and eager to fuck like a jack rabbit. Welcome to the club." I didn't believe him, but relieved to hear wasn't something else. I wanted to be sober enough to drive home. I managed a decent come-hither look and said, "While we're waiting, why don't you take me?" After going down on his hard cock, I split open a condom wrapper and unfurled it over his saliva drenched erection. I wiggled my hips as Papa grabbed my hands and pulled them above my head, pinning my hands securely to the pillow. In one spry motion, he maneuvered his hard-on into my rectum. I was pleasantly surprised by a wave of pleasure as he pumped away at me. The pills were kicking in. He planted his lips onto mine, and his tongue violated the recesses of my mouth as he thrust his cock into my asshole. He talked dirty to me the entire time; most of it telling me what a filthy slut I was. "I've heard you're selling your hot little ass after school, Princess. You're a filthy whore, aren't you?" My head swirled with excitement as I confessed, "Yes, Papa, I've been hooking on the side. I've been very bad." Oh my lord, was I enjoying myself. My penis was becoming hard yet again. Matching the rhythm of his thrusts into me by moving my hips in-sync with his gyrations, I yelled, "Please sir, cum inside me. I want it so fuckin' bad." I felt myself begin to release in concert with Papa's eruption. As I felt his pulsations, I deposited more sticky cream onto my smooth belly. A pool of sperm ran into and filled my navel. We panted heavily. I felt the sweat leaking from under my wig. I cradled myself in Papa's arms as we caught our breath. "The little blue pills are Viagra? They do wonders," I observed. Since the pills were diamond shaped, thus the nickname. "The secret to my success. I'd had less and less interest in sex for the last twenty years until a doctor offered me a free sample. I was barely able to get semi-hard until I joined the club. Now I can go a couple times a night. I've never fucked anything but women, but now I get so horny that it opened my horizons," he said as he offered me a drink and slid another diamond into my mouth. This time I swallowed willingly. Papa's face took on a diabolical expression. "Your surprise happens in about fifteen minutes. Grab your bag, get cleaned up and put on that other outfit to model for me?" I tried my best to wheedle a hint; even using a little girl pleading for candy voice, but to no avail. He slapped my ass a few times until I scurried off to the bathroom. My makeup was a mess that I hurriedly cleaned up adding even more eye shadow and lipstick. I changed to a pair of fishnet stockings, red spike heel sandals that had a single wide band with small silver studs at the toes and zip up heels. I pulled on a matching red shape hugging spandex skirt and black spaghetti strap top. I changed to a blonde wig that flowed past my shoulders. A quick glance in the mirror told me I looked like a total street hooker as my penis began to revive. Downstairs, it sounded as if Papa had turned on the television. Perhaps he was playing some porn? I sashayed down the staircase and strutted into the living room, eager to show off. Papa had remained naked, and I hoped to see him stiffen when he saw me. That is when I saw my surprise. In the chair sat a middle-aged black man. I guessed him to be in his late forties. He worn only a pair of boxer shorts that the tip of his penis poked through the slit. Papa gave me the once over. "Joe, this is my daughter, Cassi. I call her Princess. She's just home from college and become quite the little slut. She's been spreading her legs for just about anything with a cock. Hell, I just fucked her brains out before you got here." Joe's penis continued to rise out of his shorts. He was huge; at least 9 inches and thick. "She looks like a real hoe. Hey, Princess, why don't you turn around and let me check out that ass of yours?" I did as asked and my knees began to quiver. "That is a mighty fine piece of ass you have there, child." He shook his head and rubbed his cock. Papa said, "Here I am sending the girl to get an education, but she spends most of her time fucking and sucking. But you know what, Joe? They still haven't taught her to accept other races. Can you believe my little Princess has never fucked a black man before?" Joe shook his head in a mock gesture. "Shameful. It's time I schooled that ass. Come 'er, you little bigot." Using my best southern accent, I said, "Why I do declare, I'd be afraid to fuck a black man. Y'all are so big. What if my lilywhite ass-pussy can't fit that monster?" Papa commanded me, "Get down on your knees put it in your mouth." I pulled Joe's shorts off and took as much as I could into my oral cavity. His cock was dark mahogany in color and smooth, with a flaring mushroom head. I worked to get as much as possible, still I struggled with it. Papa pulled up my tiny skirt and exposed my crotchless panties. He grabbed a container of Vaseline and greased my puckering hole with two fingers, then worked in three and finally four. He glided his fingers up past the knuckles. "Your little princess is a real tart. She must be whoring herself out." "I told her she had to help with the tuition. She sells her ass on weekends." "Hey, Princess, how most do you charge for that fine piece?" I pulled Joe out of my mouth. My jaw was starting to ache from trying to engulf that nine incher. "I get $150 from all the white boys, but my ass is yours for free." On my knees, Joe gradually slid his full manhood into me doggy style. With his well build physique, he was easily able to control my pretended gestures of resistance. I was grateful that he entered me gently, but I pretended to complain in my southern girl accent "Oh Papa, his shaft is just too big for me. I can only handle those little white pricks. Have mercy, sir." Joe reached around to my thighs as he pumped away. I heard a squishing sound as he slid in and out. Papa put his cock into my mouth, and I sucked it down easily. By comparison, taking him in whole was easy. I tasted a few trickles of precum but didn't get a blast of the full ejaculation. Instead, Papa pulled out and left the room. He returned minutes later with a camera and proceed to take pictures of Joe pumping away at my ass. I felt a twinge of remorse and shame with each flash. "You can use these to advertise. I'll bet black men would pay $200 to screw your hooker cunt." Joe began to cum heavily into me. I could feel every pulse. He pulled out and removed the condom. It felt as if there was a full quart of semen in the reservoir, which he poured onto my ass. He squatted and spread his legs as Papa inserted his cock into Joe. I stood and began to stroke my protruding clitty as they watched. "Princess, put that into my mouth, I want a taste," Joe said as Papa moved back and forth. A short time later, both of us came into Joe. He slobbered the goo down the length of my shaft and onto my scrotum, where it dripped onto the rug. The three of us lay in a heap cooling off. My ass throbbed from all the attention. Papa explained that he'd tried to get together with Joe for some time, but the pictures of his whorish little daughter sealed the deal. I managed to make Papa promise he'd keep the pictures he'd taken of Joe and me to himself and send me copies. A half-hour later I cleaned up once more, still dressed in my blonde hooker getup and was about to leave. I grabbed my bag and was almost out the door, when Joe pulled me aside. He slipped me a piece of paper with his phone and e-mail. "You're gonna charge two hundred to the brothers? Couldn't I get the white-boy rate?" I winked and said, "For you, baby, I'd go a hundred, and I'm totally worth it." I kissed him once more inserting my tongue between his lips. A week later I had a doctor's appointment and scored myself some blue diamonds. I was in the club. Chapter 2 to follow... The Blue Diamond Club Ch. 02 Subtitle: A Crossdresser's Misadventures A couple of weeks had gone by since my introduction into the Blue Diamond Club. I'd been too busy with work to pursue anything more; at least, that was my excuse. If I'd been honest, I feared how much further I'd be willing to go. I hadn't dressed in anything fem since that night. Instead, I masturbated in the dark of night thinking about what I could do if nudged. That slight push arrived on Friday night when I received an e-mail from Papa. It said that Joe was hoping to hear back from me – "at least e-mail him a response," he admonished. I decided to prep myself even for the e-mail. I dressed in a short leopard-print skirt, sheer dark stockings, and a pair of strappy boot style sandals. I went so far as to put on makeup and lipstick. It seemed a bit much for e-mailing, but I wanted to feel sexy. I explained that I enjoyed our encounter, and I'd love another, but how about a different set of roles, this time out? Joe replied a short time later: Hey Princess, I'm hoping you'll play along with my little fantasy. I want a gurl like you that can meet my needs, and I have lots of unique needs. It gets me off to know I have to pay for those wants. It's not like I can't afford it. I like paying for my pleasures. I ain't no cop, just a kinky dude with BBC and an unending load. Think it over. Joe My hands shook as I typed the reply. Was I actually considering his offer? I wrote back: Joe, Couldn't we just pretend I'm your whore for the night? I can get pretty raunchy and am open to all kinds of nasty. Can go with the hooker role, but I don't need to get paid. What kind of kink are you looking for? Cassi ;-) Joe replied almost immediately: Princess, Believe me, baby, I'll make you earn every cent. Evening starts out on the town – I know a great hotspot. But you're gonna drop those panties whenever you're told. I'm also into light B&D ---> we can finish that off back at my place. You can bail anytime, but I think you'll want to stick it out. I want you, and I want to pay. Also, no condoms. I've got no bugs and test results as proof, if you can too. Buy some sexy-ass outfits for a night at the club and a dominating night in. I'll pay for those too. Joe My entire body trembled. I decided to play along, figuring I'd leave the money when I left. At least, I'd have a wild night fucking. I sent my agreement, and we made the date for Saturday. I quivered in nervous anticipation the next day, most of which I spent shopping for the right outfits. For the club, I picked out a pink fuchsia pleated skater skirt with a wet-look fabric that would flounce if I danced and a bright cap sleeve crop top that exposed my midriff. A set of chunky black platform heels completed the ensemble. For the rest of the evening, I chose an ass hugging black leather micro-mini and a rear lacing corset style top in spandex. The shoes I got were faux leather peep toe gladiator strappy high heels with a 5-inch heel. Joe was tall; we'd be at eye level. That evening Joe arrived in a metallic white Mercedes S550 sedan. I sank into buttery leather seats and crossed my legs in a feminine manner as cool jazz played on the radio. As we roared off, he told me we were headed to a gay-straight mixed club near the downtown area. We make small talk as he drove along the freeway before he pulled off after fifteen minutes. He pulled into a dark, empty side street and parked near the curb. "OK, bitch, time to start earnin' your money," he said as he unzipped his linen trousers. "Here?" "Yeah, right here. It's dark. No one's around, and the windows are tinted. Get to sucking." I pulled his stiff cock out and put my head between his legs. It looked like his rod had grown even bigger since the last time I'd seen it. Fortunately, I'd been practicing on a jumbo sized dildo since I first tried his. I handled it more skillfully this time, working the head back and forth between my lips and licking the tip as I drew in the top. Gradually, I worked five inches into my mouth and with each stoke got more of his cock into me. I'd gone up and down about twenty times; the tip seemed to tickle my tonsils, when Joe exploded into my throat without warning. Half the load shot directly down my gullet, and the rest pooled in my mouth. "Drink it down, Princess. I don't want a drop of jizz on my leather seats." He handed me a tissue, and I swallowed several times to get down the residual. It had a sweet yet salty taste. He zipped up, as I fixed my lipstick. "That's why I'm willing to pay, baby. I like to treat the crosser gurls like they're disposable. It's not you; it's just what gets me off. I'm a gay man in a sham marriage; to a woman I see a couple times a year. It works for both of us. I'm not looking for a relationship, just to do anything I want with a hired sissy. Keep a tab going and it's all good." I sat still trying to digest the last of the slimy glop I'd taken in. "OK, I know the rules now. We're all good." As we reentered the freeway, Joe told me to pull my panties off and show him my clit. I rubbed it gently as he exceeded the speed limit. I could tell he was already hard again. "Oh, you didn't think you'd get to rest tonight, did ya? When I need to bust a nut, I'm good for a gallon. I barely dropped a pint in you so far," he laughed when he saw my eyes widen. My panties stayed on the car floor when we went to the club door. The place looked like an abandon electronics factory; there were no markings on the exterior of crumbling cinderblock and brickwork. If it wasn't for the cars parked in the vacant lot next door and a line of people waiting to get in, the building would have looked deserted. Once inside, patrons were greeting by a gigantic neon club logo that said Club Serpentine Rouge, surrounding what looked like a red phallic shaped sea serpent, rising rigidly from the ocean. The back of my hand was stamped with the same emblem that could only be viewed under UV light for reentry. The music pounded out a pulsating techno beat that felt like an extended orgasm set to rhythm. It bounced off our bodies and felt like a prelude to sex. On the floor dozens gay men danced and jumped in time to the beats as multicolored beams of light shot randomly overhead. A few straight couples moved away on each other near the sides; the men rubbing their hands over their barely clothed female partners nubile bodies. Here I was outfitted like a hooker, but I was conservatively dressed compared to most of the women gyrating on the dance floor. Joe moved his mouth closely to my ear and through the pounding beats, I barely hear him say, "Welcome to the Red Serpent." I spotted a few other trannies, but recognized none of them. We had a couple of drinks as we took in the scene, and I waited to see what he wanted next. Joe moved me to the dance floor about twenty minutes later. Several gay men nodded in approval when they realized I was a male in drag. My skirt flared as I swayed in time with the seductive music. My skirt was long enough that if covered my naked crouch and ass, but I'm sure some men knew I was free of underwear. Joe grabbed me by the hand and pulled me to a staircase, leading me upstairs. A brawny bouncer in a crew cut at the top stood between us and a dimly lit battered black door. Joe slipped him a wad of small bills, and the bouncer stepped aside without uttering a word. We entered a private restroom. It consisted of a single stall and a urinal, but was otherwise deserted. Joe removed his pants and motioned us toward the stall. "Com' on, Princess. I got us ten minutes." I knew what he wanted; I'd seen 'American Hustle'. I was about to get fucked in a toilet stall. I moved to walk inside. "No, baby, me first." Joe bent over, leaned on the john and pointed his ass toward me. "Go on, put your prick in me, bitch." He looked over his shoulder impatiently. "Yeah, that's right, I need my ass fucked. Get to pumping. That's what I'm paying you for." I grabbed his shoulder and worked my way into him. His asshole had been well stretched; becoming an easy entry. He bent over as I pumped against his buttocks. He cursed loudly with pleasure, but with the abundant musical reverberation, it would never be noticed. "Ah, fuck yeah, drill it." I moved one hand down to stroke his cock and balls. I squeezed hard as Joe whimpered with agony and delight. He shot a stream of spunk over my hand shortly before I came inside his puckering asshole. We stood to see two men peeking over the door of the stall, grinning like morons. "Sorry, but we slipped past the bouncer. That was marvelous. You two are a delight," one said as he pulled out his cock, and the other man dropped to his knees and began a blowjob. Joe grumbled about nobody respecting privacy anymore, as we returned downstairs. He handed me a twenty and said, "Buy yourself a drink. I need about fifteen minutes alone." He started to walk away, but stopped and said, "Take one of those blue diamonds. I want you hard." So he knows about the Viagra. I guess it wasn't any great mystery. I hadn't seen him take any, but I was just his whore for the night. It was none of my business. I sipped an energy drink and fended off a few guys hitting on me. Too bad, some were cute, but I was on the job, so to speak. I could always come back another time. It took twenty minutes for Joe to return. He was accompanied by a massively large black male that I assumed had to be a young pro-football player. I had no idea who he was, but other men glanced his way. Joe addressed him while barely looking toward me. "This is Cassi, the Princess I was telling you about. Want to take her for a spin? Wear a cover." The footballer nodded, and Joe dropped his keys into the man's gigantic hands. I started to stammer that I hadn't planned on this part of the deal, but something told me I'd better play along. The footballer put one of his enormous paws on my ass and rubbed it as we headed toward a side door. "Joe seems in a mood," I observed. "He's calling himself Joe tonight. Good one," the footballer laughed, "Yeah, Princess; he doesn't like to speak to someone that's just fucked him for a while. Don't take it personal. He likes his space. By the time I'm done with you, he'll be a gentleman again." The back door of the Mercedes was opened, and I was placed on my knees onto the rear seat with my skirt pulled up. He spit on my crack for lubrication and shoved his hard cock into my waiting hole. Despite his size, his cock wasn't as thick as Joe's, but roughly the same length. His hair had been done up in small braids and pulled back into a ponytail that fell into my face as he began to move his cock inside me. The entire car seemed to rock as he banged away. My own cock was getting stiff from the attention and the effects of the blue pill. I lost track of time and sensed the slithering sensation of this unnamed stranger's cock gliding through my rectum. He finished with a couple of sharp pushes that nearly knocked the wind out of me. He pulled off the condom and dropped it onto the cracked pavement. The lot was likely full on used condoms. I watched my step as we headed back to the club. I managed to grab my panties from the front of the car and pulled them back on after we returned to the club. At least, the footballer expressed his appreciation of our activity. Joe smiled as I walked toward him. "Did you show my man a good time?" "He enjoyed himself," I said in a clipped icy tone. "Oh, come on now baby, don't be that way. I wouldn't offer you up to him if you weren't something special. There's things I have to do to get along in life. Providing the finest tranny ass is a part of it. Believe me, you are worth the investment." "This isn't a game, is it?" "Not the one you were thinking. I told you, you'd earn the money. It's all good, right?" I calmed myself. Tonight I was the prostitute, for real. I vowed I'd never do this again, but there was no other way home. I'd go along, as long as I had too. I smiled sweetly back at Joe. "It's all good, sir. I forgot my place; that's all." "That's fine. You get double for my man. Keep that tab running." Chapter 2 to follow... The Blue Diamond Club Ch. 03 Subtitle: A Crossdresser's Misadventures I wanted to ask Joe or whoever he was, what he did for a living, but knew I'd never get a straight answer. Better to go with the flow. I mentally counted the sex acts I'd performed thus far. Blowjob, ass fucking, getting fucked. We hadn't bothered to negotiate a rate for any of these. It'd be poor etiquette to bring it up now; I wished I'd covered it in the e-mails. Wait, I'd joked to Joe two weeks ago; I'd only charge him a hundred dollars. My ass was worth more than that. Jesus, now I was really thinking like a prostitute. We hit the dance floor again, then came another trip to the private restroom. This time I was the one bent over the toilet. Being fucked in a public lavatory isn't nearly as sexy as it seems in the movies, but I figured it earned me another hundred bucks. This time, it was only ten minutes before Joe wanted to speak to me. I felt a trickle on his sperm leaked from my anus to the back of my panties as I waited seated on a bar stool. We left soon after, and I realized I wasn't going directly home. That leather dominatrix outfit I'd gotten at Joe's instance was still waiting, and I was sure I'd be doing more than modeling it for him. Joe's house was large and surrounded by a very tall, very private wall. The Mercedes entered through an automatic iron gate. The decor of the place was sufficiently tasteless to say that Joe had money, but hadn't come by it that long ago. By then, I was letting my hard cock do all the thinking for me; purposely disengaging my brain as much as possible. I changed into a patent leather mini skirt, the strappy gladiator high-heeled sandals, dark stockings supported with a flimsy garter belt and corset top. I finished the look with dark-brown smoky eye shadow and a jet black Betty Page style wig with straight cut bangs that went just above my eyebrows. Only the red lipstick kept me from looking too Goth. I found my way to Joe's "entertainment room," a large windowless expanse at the center of the house. The walls were lined with large screen monitors that, even at this hour, played a variety of sporting events from around the world. A half dozen matching leather theater style sofas provided ample viewing comfort. A raised platform about a foot high along the front bank of monitors provided an open space beneath. The only object on the platform was a large X shaped contraption. It stood about six feet tall and as my eyes grew used to the low light of the room, I noticed chains and manacles attached to each corner of the crux. A spotlight began to highlight the cross as the rest of the room went darker and the monitors dimmed. "Do you like my little play area?" Joe asked from the front-most seat. Without turning my head toward him, I replied, "It depends, is it you or me that's supposed to go up on that rack?" He laughed heartily. "Drop them panties and get your ass on the stage." I had my answer. I slowly slid them down my legs pointing my ass toward Joe. I tossed them to him and assented the single step, so I stood next to the cross. I faced him with my erection poking out from under my tiny leather skirt. With the glaring beam of harsh light highlighting the cross, I was no longer able to see his face. Gradually, the sound of techno music began to play. The rhythm was more erotic than what I heard at the club as short time ago. I wasn't sure if I was supposed to dance to it, so I remained in place as expressionless as possible. Joe remained silent. On the side of the room a heavy dark oak panel door opened and five men entered. I saw that two were black, two white and one Asian, before they disappeared in the darkness of the seating area. A few talked in low, hushed tones among themselves, but became silent once seated. The door opened again and in walked a woman dressed in a long black leather skirt and low cut bustier that held up her abundant breasts. She wore a military-style leather biker cap with a broad brim that obscured her eyes. When she stepped onto the platform next to me, she nodded her head slightly, and I heard applause from the seating area. She had on elbow length gloves and grabbed my chin between her thumb and index finger as if examining my face. She stared into my eyes with a frozen gaze before releasing me. In her other hand, she held a riding crop that she used to poke at my erect penis; pushing it to one side, then allowing it to bounce back in place. Facing the men, she reached toward her back and undid a snap in the back of her full-length skirt. It fell to the floor and exposed a large erection. Her penis must have measured eight inches and her pubic area was entirely shaved except of a half-inch wide patch immediately behind her penis. I made a noticeable gasp as I realized this was not a woman, but a fully functional transsexual. I heard a few snickers, then more clapping from the audience. Her dark auburn hair was her own, not a wig like mine. Her face was lean and harsh, with a thin pronounced nose. I felt outclassed. Clearly, my role was to be the "victim" in this little spectacle. "I am Mistress V. You shall have no name. You don't deserve a name," she said in an overly dramatic Eastern European accent. She slapped me across the ass with the crop which made a loud crack as the slap on the tip connected with the flesh of my ass. I felt little pain, since the crop was designed to produce a snapping sound and not inflict suffering to the animals it was supposed to be used upon. I pretended to wince. Mistress V pushed me toward the X crux, forcing me to face the frame and placed the padded shackles on each hand, then my legs. I heard only the clicking of her spike heels studded pumps across the wooden flooring and felt her harden penis rub against her exposed buttocks. I realized that I was then completely at her mercy; her expression said that the Mistress had none. Mistress V brought out a wide rectangular paddle and showed it to me. Like the tip of the crop, it consisted of two flat strips of leather. It would make a loud sound as it contacted its target. I looked down at my erect penis below the cross joint. "I can cause you to have pleasure," she announced in a commanding nearly feminine voice. With that I heard a pronounced clap against my ass and a slight tingling sensation. "Or I can cause you to have much pain." She turned the paddle around, swung harder and more force. It made a sharp crack that reverberated throughout the room and I felt a wave of pain on against my posterior. I screamed in shock as a jolt of torment overtook me. In rapid succession, she turned the paddle over with each blow alongside my reddening bottom, striking with a practiced expertise of a true member of her craft. "Pleasure or pain, pleasure or pain. Pleasure or pain? Do you understand?" Between my screams, I blurted out, "Yes." "Yes, what?" Another rap crashed across my buns. "Yes...yes, Mistress." I looked down once more. My erection was dripping a thin strand of semen. I looked up to the monitors. The sports matches were gone. They had been replaced by views of me shown in different angles. To the right, was my face expressing my humiliation and suffering, to the far left was my crimson ass betraying outlines of the paddle and in the central monitor by leaking penis. I heard cheers as my dribble touched the floor. "Who wants this one?" she called out to the crowd. "Is there none among you that will take this unworthy object for your pleasure? She is nothing more than a common prostitute. Are all of you that shy and afraid to be first?" No one came forward. The crux began to be rotated parallel to the floor by the Mistress and lowered to two feet above the platform. I lay flat on my belly, tightly bound and helpless. "Very well, I shall be the first," I heard her announce, then spit onto my ass split several times. I watched on one of the monitors as she unrolled a black condom over her hardness and in one, fluid motion penetrated my rectum. She thrust into me, and I began to forget the agony my ass had endured. "Does this bring you pleasure?" "Yes, Mistress. So much pleasure." "Do you prefer the pain or do you prefer the pleasure?" "The pleasure, please, Mistress." "Is there no man here to give this one the pleasure?" She paused for several seconds. "Or the pain?" One man stood and walked to the platform. The Asian man was already naked and hard. After Mistress V pulled out of me, she placed a condom on his cock and he proceeded to stuff it inside my asshole. I heard shouts and whistles as he rocked away on me. Mistress V flicked me periodically with the riding crop; sometimes on the legs or back, a few times directly across my cock and balls. A pleasure mixed this the occasional sting of pain. The Asian man finished and I felt his load eject into me. He pulled out and removed his sperm-filled condom. One of the white men appeared next wearing boxer briefs and I readied myself for another anal invasion. Instead, he took the paddle in hand and threw five quick raps against my tartish butt. He'd used the gentle side, but with my already sore posterior, I felt a wave of electric ache shoot through me. He masturbated himself over my head and soon shot a load into my face. The goo dripped off my nose and ran down to my chin. One of the black men and a white man joined me on the stage. They were completely naked and had their arms around each other. They kissed passionately before the black guy guided his partner's penis into my mouth. I sucked as best I could, given my constrained position. The black man began to rub against my ass crack without entering. They matched the cadence of their motions and within five minutes, came simultaneously. I let the semen dribble from my mouth and felt a warm pool of spunk soak through the material of my corset top. The other black male was soon on stage and in my asshole. He pumped me and slapped my ass with a bare hand, being sure to find the most sensitive marks left by the paddle. I pleaded for him to stop, but he had no sympathy for me. I was a whore after all, he kept reminding me and whores do what they are paid to do. He yelled as he came, "You fuckin' cheap hoe. Take it all, you filthy bitch." I ached and was exhausted. I begged to be released by the Mistress, but she had other plans for me. She began to massage my erection and stroke my balls as she rubbed her own erect member over the cheeks of my ass. I came in a torrent, my full load spilling onto the floor into a pathetic milky white puddle. "There is one last man here that must provide the pleasure or provide the pain." Joe remained in his seat several minutes before arriving to cheers. He removed his clothing. He didn't bother placing a condom on his hard unit, again preferring to insert himself into me bareback. He hammered away for fifteen minutes as the rest of the men cheered him on, grunting in regular intervals. He came in a sudden blast inside me and even after he'd pulled out continued to shoot his cream over my ass. "Oh, yeah. That was the best one I had tonight," he bragged to his associates. He and the rest of the men swiftly gathered their belongings and exited through the oak side door. I was left alone on the stage with Mistress V, who released my bindings. She handed me a towel and my bag, pointing to a bathroom where I could clean-up. She retained the accent and character throughout our brief conversation, and I realized it wasn't an act. "There will be a taxi arriving at the front gate in twenty minutes. Your fair and gratuity has already been taken care of. This is also for you." She handed me a thick plain white envelope. I glanced inside. It contained at least two-thousand cash in hundred-dollar bills. I frowned and shook my head. "Do you feel it is not enough? There was the man you call 'Joe' four times, his friends at the club and his five friends tonight, along with your show for us, reimbursement for your clothing plus a generous gratuity." Again, I shook my head. "No, I'm not a prostitute. This was meant to be a fantasy. All pretend. We were supposed to be having fun." I dropped the envelope to the floor. The Mistress' hand moved to my chest as I made my way to the bathroom. "And it was fun for you?" "No. It isn't what I expected." "Yet the man and his friends enjoyed themselves. You pleased them. It was work that you performed." She stooped at the knees, displaying her statuesque legs lovingly surrounded by black nylon, and picked-up the envelope, handing it back to me. I noticed that her penis was still completely erect and had remained that way since she first entered the room. "We all are paid for things that we do called work. Only a fool would do otherwise." I swallowed and took the envelope. I watched as the Mistress exited the room, her erection still protruding prominently. Twenty minutes later I was seated in the back of a cab, dressed in the male clothing I'd brought. I made no conversation with the driver, instead pondering if I'd toss the bag of my evening's clothing into a dumpster when I reached home. With what remained of Sunday, I slept the remainder of the day and into the next morning. When the alarm rang bright and early, I wasn't ready to rise or shine. My body felt limp, but not nearly as much as my exhausted penis. My ass was on fire and my rectum raw. A rush of shame went through me when I spotted the envelope of money still sitting on the dresser. I called in sick to work and blacked out until the late afternoon. A warm soapy shower revived me to some degree. I stumbled to the kitchen as I was famished. I hadn't eaten anything but sperm in the last twenty-four hours and my belly reminded me of the abuse it'd been put through. I noticed the bag of spunk drench slutware still sitting by the front door. I didn't check e-mail until Monday night. Good; none from either acquaintance from the Blue Diamond Club. I had no further plans for Joe and hoped he didn't have any for me. My cock wasn't talking to me at the moment, much less doing any thinking. I pondered the direction I'd been going with my life. Maybe tarting myself up on weekends and looking to get fucked wasn't a long-term solution. I considered myself bisexual. I'd fucked a bunch of women in my time – cute ones, hot ones, really dirty ones; although I hadn't 'found time' for a girlfriend in a while. I liked women. In fact, I like them so much I enjoyed being one on occasions. I downed a beer and decided to drop a Blue Diamond; just to see if my cock still functioned. Well, yeah, in twenty minutes my erection was back to life, and I pulled on a pair of sheer black panties. I imagined my penis, saying, "Good God; I can't believe you actually sold your ass and so many times, you fucking slut," as it got harder and harder. "Stop abusing me so much." With that, I tossed what remained of by blue diamonds into the trash, and I permanently revoked my club membership. This time my cock talking to me seemed to make perfect sense. The End