The Blue Diamond Club Ch. 03

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Crossdresser's role playing has unexpected results.
2.8k words
4.15
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8

Part 3 of the 3 part series

Updated 10/19/2022
Created 09/17/2014
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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

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AnonymousAnonymousover 9 years ago

Interesting series. Nice to read something a little different.

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