Chicago Bound Ch. 02


This is another installment in the ongoing saga of a couple who met in the original story, “Fourteen Days on the Mountain”. In this story, the third since the original, Mike, now 29, and Tiffany, a 20 year-old blonde, have a wild time visiting their friends, Paul and Kelly, in Chicago. For a more in-depth and intimate knowledge of the characters and chronology, read the aforementioned original story, followed by “The Move” and “Santa Monica Swing”, then part one of this story.

Before you read this story, be advised that it is adult oriented and contains very graphic depictions of a sexual nature. It is not intended for, nor should it be read under any circumstances, by persons who are not at least eighteen(18) years of age.

I love to read your comments and would enjoy hearing from you if you like this story. I even want your comments if you don’t like it, provided you are actually giving constructive criticism. Please don’t leave a comment if you are simply turned off by what the story contains. Just because you may not enjoy or politically agree with the portrayals, it doesn’t mean that others won’t.



As Kelly caught her breath, Paul picked up the phone again. “Yes… White tray for four, please,” he said, and hung up.

Reaching behind me, I let my fingers find Tiffany’s nude body as she snuggled with me. “I guess you had a good time,” I stated rhetorically, twisting my head and looking at her over my shoulder.

“Mmmmm… You bet I did,” she responded, letting her right hand slide lower to find my wilting tool. Gently stroking it, she asked, “What about you?”

“Yeah…” I said, “I had a great time.”

“But…” she posed.

“But what?” I asked, puzzled.

“It just sounded like there was a ‘but’ coming. Is something wrong?” she wondered.

“No. Nothing. I just haven’t quite recovered yet,” I pretended. Although, I guess if I had been honest, I was still a bit concerned that Tiffany was going to get some wild idea that she could dominate me in bed. I just couldn’t get the idea out of my head, knowing it would be a bad scene if she tried.

I heard a knock on the door and it opened. In came the same waiter that had delivered our drinks earlier. This time he was carrying a large sliver tray, covered by a dome. He didn’t even seem to pay any attention to the fact that both of the females were nude, or that Paul and I both had our dicks hanging free. Setting the tray in the couch, he asked, “Will there be anything else, sir?”

Paul told him, “No. That’s all. Thank you,” and handed him another tip.

The waiter exited, closing the door behind him. When he was gone, Tiffany giggled her patented schoolgirl giggle and snickered, “Great service here.”

I figured that Paul must have ordered us a snack, but didn’t want to assume anything at this point. “What’s that?” I queried.

Paul reached over and removed the covering. Under it were eight white towels, four hot, damp ones in plastic bags, and four dry ones. “You don’t want to walk around all sticky do you?” he inquired. Going on, he extended, “Just another one of the ‘perks’ that makes this club so nice.”

We each took a damp and a dry towel to clean up a bit. As we wiped down, Paul offered, “If we hurry, we still might be able to visit the slave, if you’d like.”

A little confused, I questioned, “Do what?”

He explained that after each performance, the slave is put on display for everyone’s inspection. He told us that it was kind of a ‘meet the actors’ type of deal, but also served the purpose of proving the severity of the on-stage punishment. “Sometimes the dom, or doms, as it would be tonight, are there too, but it’s usually just the submissive,” he said.

“Come on,” Tiffany urged, “I want to see this chick close up.” We hurriedly finished our clean up, and began to dress. “Huh-Uh, not you!” Tiff directed Kelly. “You need to stay naked.” Then she turned to Paul to confirm, “It is appropriate to keep a slave naked, right?”

“Yes, but she’ll have to wear this,” he replied, pulling a collar and leash out of his jacket pocket. “The rules are that no one is allowed to be totally nude in the common areas, but a collar and leash are acceptable.” Offering the items to Tiffany, he asked, “Would you like to…” Before he could finish, Tiff had snatched them from his hand and was headed toward Kelly.

Kelly didn’t say a word as Tiffany fastened the collar around her neck, simply stood there obediently. Snapping on the leash, Tiff let it drop between the sub’s breasts, the loop handle hanging below her furry mound. Stepping back to admire the slave, Tiffany oozed, “That looks sooo hot…”

“Just so you know; She hates to be paraded around here like that,” Paul told Tiffany. “I’ve used it as a mild punishment a couple of times, but I’d bet she considers it a treat tonight. Especially if you’d be willing to handle her leash, my dear.”

“Is that right…” Tiff replied? “Would you like me to lead you around, slave?” she boldly Bostancı Öğrenci Escort questioned the now blushing woman. Tiffany seemed to be really getting into her role as dominatrix, and I had to wonder just how far she would take it. “Well, slave…” she barked, reaching down to take the loop of the leash, “Would you like that?”

Kelly nodded her head in the affirmative, flashing a wide smile at my girl. That settled, we headed out the door and Paul led us through a series of corridors and turns. We descended a couple of flights of stairs and rounded another corner, bringing us to an area the club members referred to as ‘Misery’.

Paul explained that the term was originally derived from the state name ‘Missouri’, which is called the ‘show me’ state. Someone apparently thought this appropriate because members would come down here and demand to be shown the marks on the slaves. As this became regular practice, it also became evident that this was a place of humiliation for many of the subs, hence the ‘misery’.

There were several people gathered around, obviously ogling the unfortunate victim of the performance. We worked our way toward the front, being met with a velvet, theater-style rope barrier. The two hooded men who had assisted on the stage were standing on either side of the slave, and a bright light shone down on her. She was facing us and you could see that the blindfold was still in place, and her torso was splotched with varying shades of pink and red.

I could see bits of hardened wax still clinging to her skin in areas that the crop had missed. There was also an abundance of waxy buildup in the ‘mohawk’ of hair covering her pubic mound. It was more concentrated in the lower portion of her bush, as it disappeared between her tightly closed legs. Apparently this was the remnant of the candle she’d held in her pussy while the ‘master’ had beaten her with the bullwhip.

“Turn her around, please,” Paul requested, and the two men spun the girl around to display her backside. Her back and buttocks were splotched red, like the front of her body. And, there was more wax visible in the cleft of her ass, again disappearing between her legs. But, angling across her posterior were wide, deeper crimson stripes that highlighted the raised welts left by the whip. There was no mistaking that the punishment had been very real indeed.

“Can I touch her?” Tiffany asked Paul in a hushed, but almost hyper, tone.

“No. This is an ‘eyes only’ display. But, if you want, I could try to arrange a private meeting,” he replied.

“That’s okay. I don’t want you to go to any trouble,” Tiff told him.

“Show’s over!” one of the hooded men bellowed, then directed the sub, “Come on, wench.”

I looked over and found Paul huddled with the second of the hooded attendants. “Wait here,” the guy told Paul and then disappeared through a door, following the slave. A few moments later, the door opened again and the ‘hood’ returned. “Follow me,” he gruffly instructed as he unhooked one of the velvet ropes.

We proceeded through the door and into a hallway, then were shown to another door. “Master Wolfe is waiting inside,” the man told Paul.

“This is an unusual occurrence, so just follow my lead,” Paul told us, “Remember that she is his property; treat her as such.”

Upon entering the room, we were greeted by the last of the men who’d doled out torment on the submissive girl. He still wore the dark glasses, and looked even more daunting, now that we were up close. I had a feeling of nervous excitement deep in the pit of my stomach, wondering what was in store for us.

The fellow stuck out his hand, greeting Paul with a surprisingly cheerful, “Hello, I’m Master Thomas Wolfe.”

“Good evening, Master Wolfe,” Paul extolled, “We truly enjoyed your performance.”

The dark figure responded, “I’m glad you and your guests found it entertaining. Did your slave like it as well?”

“I’m sure she did,” Paul told him, nodding at Tiffany.

My baby didn’t miss his cue and tugged at the leash, inquiring, “Well, slave, did you enjoy Master Wolfe’s performance?”

Kelly nodded her head, almost imperceptibly, and meekly replied “Yes, ma’am.”

“Very good!” the ‘master’ approved. Then turning his attention to Tiffany he said, “I understand that you are a budding dominatrix, my dear. And that you would like to touch my pet. Is that correct?”

“Yes. That’s right,” she told him.

He thought for a moment and then bargained, “I will let you touch mine, if I can touch yours.”

“She’s not really mine to trade. She belongs to Paul,” Tiffany explained.

Paul quickly spoke up, “For the rest of the weekend, she’s yours to do with as you wish.”

I saw a demonic twinkle light up the blonde’s eyes, and knew that she was hooked. “Master Wolfe, I agree to your offer…” she began, and I could see Kelly immediately begin to tremble. Going on, Tiffany added, “With the understanding that this is touching Bostancı Çıtır Escort only, and no punishments allowed.”

“Agreed,” Wolfe said, stretching out his arm and hand toward his slave girl.

Tiffany dropped the leash and moved to the punished form of the still blindfolded female. Her hand reached out and she let her fingertips lightly glide over the swollen stripes on the girl’s hind-end. The sub flinched slightly when she felt Tiff’s touch, but remained motionless after that. I was amazed at how transfixed Tiffany was by all of this, and the big question of what she intended to do with her new hobby was growing in my mind.

Master Wolfe neared Kelly and she continued to tremble, even though he had agreed to Tiffany’s ‘no punishment’ terms. He circled around her, surveying her curvy frame a couple of times, then paused behind her. One of his hands came around her body and he cupped one of her breasts, lifting it slightly. His fingers moved forward and came together on her silver-studded nipple, then moved away.

“I’ll bet that you’re quite the horny little bitch,” he muttered. “I’d even bet your pussy’s wet right now,” he continued, speaking almost in a whisper. Then, as he ran his hand down her back and over her shapely ass, he growled, “I’d enjoy putting a few welts on this fine ass of yours, slave. That would get your pussy all wet, wouldn’t it slave?”

I noticed Kelly shudder and saw her skin break out in a rash of goosebumps. “Y-yes Master Wolfe,” she quietly responded.

“Spread your legs slave,” he commanded her. “I want to see if you’re telling the truth.”

Kelly obediently shuffled her feet apart and the man slipped his big hand between her thighs. He brought it up and back, letting his middle finger slide between her pussy lips. “I guess the thought of me whipping your ass does please you,” he commented in that same low and quiet voice. He looked at the glistening pussy juice on his finger, then bluntly directed, “Clean it off,” placing the finger on her lips.

She sucked it clean and then Master Wolfe moved away from her, toward Tiffany and his own sub. “Well, what do you think Mistress…” he questioned, trailing off, not knowing her name.

“Mistress Tiffany,” my darling told him, still running her fingers over the slave’s whip-marked body. “Very nice. I think our pet over there would look better this way, though.”

I think Paul and I both were shocked to hear her seemingly offer up Kelly for such harsh treatment. But, before either of us could protest, Tiffany gracefully, and literally, saved Kelly’s ass. “But we will have to do it some other time. There is much more here to see tonight, and I’m getting a little tired,” she demurely explained.

“Very well,” the man replied, “Here’s my card. Contact me when you’re ready.”

“Thank you for your hospitality, Master Wolfe,” Paul lauded, moving toward the door.

Tiffany returned to Kelly and picked up the leash. “Yes. Thank you, sir,” she echoed.

“You’ve got a good start, Mistress, but let me give you some advice,” Master Wolfe said. “You just made your first mistake of many to come. Never address another dom as sir or ma’am; use their titles. Always remember that this scene is as much, or more, about etiquette than the pain.”

“Thank you again, Master Wolfe,” Tiffany corrected herself, and we exited the room. Moving quickly down the hallway, we were soon back in the corridor that housed ‘Misery’. Paul pointed to his left and we set off.

“Wow, that was tense,” Tiffany remarked, tugging at Kelly’s leash. “Did I have you worried, my little pet?”

“Yes Mistress. I don’t think I could take his whip,” Kelly responded.

“Well, we’ll see how you do under mine,” the blonde vixen taunted, now fully aware of what this weekend was about, and totally accepting her role.

Paul led us on a tour of the facility, which was a good deal larger than it appeared from the outside. Most of it was housed underground, leaving the aboveground part looking quite normal. He turned a corner and stopped at a closed door. Another keypad guarded the entryway and he typed in a number. I heard a ‘click’ and Paul opened the door.

“This is ‘Voyeur Vista’,” he informed us. “Just as a warning, there’s no telling what you might see in here.” He then expounded, as we filed in, that this corridor was lined with one-way glass which served as a wall in some of the rooms. “These rooms are for people who like to be watched, yet still want some privacy.”

As we made our way down the corridor, we saw all sorts of sexual depravity being practiced. And it wasn’t all whips and chains either. One room had a guy dressed up in a diaper and some woman playing ‘Mommy’ to him. Another one was set up like a classroom and there was a female, complete with school uniform and ponytail, blowing a much older ‘teacher’.

For the most part, though, these rooms were a mixed venue of S Men dominating women, women dominating men, women on women, and Bostancı Elit Escort so on. In one room we witnessed a dominatrix fucking a male sub with a strap-on dildo while she forced him to suck off another male slave.

After a few minutes, she made both of them lie down on the floor, head to toe on their sides. She commanded them to suck each others cocks and then she climbed onto a platform about two feet off the ground. From there she started pissing all over both of the poor schmucks while she berated them verbally.

That scene once more stirred up my uneasiness concerning my girl’s newfound persona. I guess Tiffany could sense my unrest. She sidled up to me and whispered, “What’s wrong Baby? Don’t you want me to fuck you up the ass and then piss all over you?”

Looking into her eyes, I could tell she was simply teasing me. But I was still concerned until she confessed, still whispering, “Don’t worry. I’m not interested in dominating you, even if I thought you’d let me.”

Her words lifted the weight of my concern, but still left me curious as to how far she wanted to take this whole domination script. I was happy with the lifestyle that we had, sexually speaking. And while I’m always open to new adventures, I wasn’t looking for a complete change. My hope was that this would be a ‘once-in-a-while’ pastime.

We continued the tour, stopping in the communal ‘playground’, as Paul called it. This area was as big as a basketball court and had small dining tables dotted throughout. We sat down at a vacant table and Paul motioned for a servant.

A female trotted over wearing a leather outfit, consisting mainly of nothing but a bodice. Her hefty tits were bare and hung over the top of the garment, her shaven pussy clearly visible below. Other than that, she had on a leather collar, complete with dog-tag, and a pair of fishnet hose.

“Yes, sir. What would you like?” she asked.

“Four rum and cokes,” Paul answered and the girl turned to fetch our drinks.

As she walked away, I noticed that she had a long tail dangling from her backside. It hung down to mid-thigh and swished from side to side as she walked away in her spiked heels. I’d seen these in a couple of sex shops that Tiffany and I frequented, but like a lot of the toys in these shops, I never took them very seriously.

“Is that tail attached to…” I paused, for some unknown reason not wanting to seem crude.

“A butt plug?” Paul chuckled. “Yes, my friend, it is.” Paul went on to explain that most of the servants in this area were slaves on loan from their masters. He said that this was usually a form of punishment. Kind of like working off a debt. “If a girl is wearing a tail, it usually signifies that she was unwilling to accept anal play,” he said. Then, almost boasting, he added, “But our pet, Kelly, has never had to wear a tail when she has served here.”

Elaborating, he told us that we were allowed to touch and inspect the servants, among other things. He pointed at another table and I could see one of the servant girls busily bobbing her head in a patron’s lap, obviously blowing him. “Of course, this is all done with the respect that you would have for any property that someone has lent you,” Paul said, nonchalantly.

“So Kelly has done this?” I asked as the servant returned with our drinks.

“Yes. A few times,” Paul replied, then ordered the servant girl, “Show my guests how your tail stays put, harlot.”

The well built, thirty-something female promptly put the tray on the table, turned around, bent over and pulled her butt apart with her hands. Sure enough, there was a bright red butt plug seated firmly in her anus, the several dozen thin strands that made up the tail encased in its body.

“That’ll be all, slave,” Paul said, and the girl stood up, wiggling her bottom a little to readjust the tail. Then she took the empty tray and hurried off to another table.

“That’s so cool,” Tiffany chirped. “Did our pet have to do anything special when she served here?”

“One time I made her walk around with a big rubber dildo in her mouth,” he began. “I caught her blowing another slave without permission, so she spent the rest of the evening serving drinks with this big fake dick hanging out of her mouth, and the word ‘whore’ written across her forehead.”

“Did you enjoy that, my pet?” Tiffany asked sarcastically.

“No, Mistress,” Kelly replied.

I don’t really know why, but the sound of Kelly referring to my sweetie as ‘Mistress’ was amazingly erotic.

“Do you like calling Tiffany ‘Mistress’?” I questioned her.

“Ohhh, yes, Sir!” was her animated reply.

“Why is that, pet?” I pressed.

“Because she is so young and sexy, Sir. And because I really enjoyed having sex with her when we were in the mountains last year,” Kelly bubbled, but quickly regained her simplistic posture.

“Stand up and come over here,” I commanded, and Kelly readily complied. “Does thinking about Mistress Tiffany dominating you make you all wet?” I teased.

The sub sheepishly nodded her head and I said, “Let me see.” She slid her feet apart, opening her legs wide enough that I could get my hand between her thighs. I reached out, bringing my fingers up and into her crotch, my touch raising the goosebumps on her skin once more.