Chicago Bound Ch. 01

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Mike and Tiffany visit Chicago for some B&D fun.
7.5k words
4.49
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Part 1 of the 2 part series

Updated 09/22/2022
Created 08/24/2008
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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 then "Santa Monica Swing".

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.

~~Odysseyker

*

About five months had passed since Tiffany's birthday, and we'd settled into a very comfortable cohabitation. Almost too comfortable it seemed. Tiffany and I had opened our bed to a number of partners in that time, and we shared our passion with Cheryl, Tiffany's step-mom, frequently. But I sensed that something was not quite right with my little blonde sweetheart.

I discussed the issue with Cheryl, to see if Tiffany had confided any problems to her. She told me her daughter hadn't, but she had noticed that something was a little off with Tiff. We talked about what could possibly be wrong, and I finally came to the conclusion that our routine had become just that, routine. Tiffany had a lust for life and excitement, and while our lovemaking was hot, and as good as ever, we hadn't done anything lately to shake things up.

The one-year anniversary of our first meeting was approaching, so I decided that would be a good time to try and provide a little spice for Tiffany's enjoyment. We had remained in contact with Paul and Kelly, the married couple we'd met on our mountain vacation. Through the e-mails that we received, I was aware that Kelly had become quite the submissive little slut. This was a role that Tiffany and I had helped initiate her into, on that same vacation.

Remembering the gleam in Tiffany's eyes after she belted Kelly a couple of times with a riding crop, I knew that she would enjoy the opportunity to really dominate the woman. There was a good probability that I could have arranged something similar right there in Santa Monica, but I decided the change of scenery might be nice. And besides, I guessed that Paul and Kelly would be happy to see us again; They had invited me to come to Chicago, after all.

I phoned Paul and explained the situation to him, and he said that they would be thrilled to have us come and spend the weekend with them. He assured me that he would have something special set up, and that he was certain Kelly would love having Tiffany dominate her. We made all the necessary arrangements and said our 'goodbyes'. By the time I hung up the phone, my dick was about half hard from my thoughts of how the weekend might play out.

Tiffany's eyes lit up when I informed her that we were going to visit Paul and Kelly to celebrate the anniversary of our meeting. She was a little disheartened when she found out that Cheryl wouldn't be accompanying us, but was fine after her mom let her know that she already had other plans.

Friday came and we set off for the airport, and Chicago. Paul was waiting to pick us up at O'Hare, and Tiffany greeted him with a hug and kiss. "Where's Kelly?" the twenty-year-old nymph asked.

"She's still at work," Paul replied, "She should be home by the time we get there."

On the ride to their suburban home, Paul told us that he had made reservations for us to go out to dinner, and then to see a show. It sounded pretty tame, and I could tell that Tiffany had hoped for something a little more exciting. I suspected that Paul had more in store for us than he was letting on, though. He went on to say that he and Kelly had seen this particular show before, and was sure that we'd enjoy it.

When we arrived at their house, Paul informed us that Kelly was indeed home, motioning toward another car in the driveway. Upon entering, Paul called out her name, with no response. "She must be taking a shower," he mused. And, as we quickly found out, that was the case.

I had no more than set our suitcase down when the bathroom door opened and out came a nude Kelly, toweling her hair. "Oh hell!" she yelped in surprise. "I didn't think you guys would be back so soon," she stammered, obviously a little embarrassed, but not enough to cause her to cover up. She simply hugged each of us, lingering a bit longer with Tiffany than she did with me.

We quickly dispensed with the usual "good to see you" pleasantries. And while we did, I took note of the fact that Kelly's previously unshaven bush was now trimmed into a neat, but still thick, triangle. She also sported a pair of silver studs, one through each nipple, shining brightly against the dark skin of her areolas. Her plumpish figure was the same as it had been a year ago, and there were a few light bruises that marked her body, in areas indicating they were the result of some rough sexual play.

"Why don't you show them to their room, and I'll go get dressed," Kelly suggested to Paul, then she scurried off. Paul escorted us to the guest bedroom, at the opposite end of the house. He told us that we had about half an hour before we needed to leave for dinner, and that we should dress 'nice, but casual'. Tiffany and I quickly unpacked and freshened up in our private bathroom, then changed for dinner. Just as I was slipping my shoes on, Paul knocked on the door to see if we were ready.

Dinner was nice and we enjoyed catching up on what had transpired in each other's lives over the past year. But, by the time we'd finished eating, I could tell that Tiffany was getting a bit restless. I hoped that whatever this 'show' was that Paul had booked us for would be captivating enough to keep her mind occupied. I don't think she was really in tune with the fact that Kelly had become so submissive, or that my whole plan was to let her play the dominatrix. But even so, I knew Tiff was ready for a good romp.

Paul asked the waiter for the check and told us, "We better get going or we'll miss the start of the show." When the check came, I offered to pay for all of our meals, but Paul wouldn't have it. "No way! You're our guests this weekend," he admonished. "We intend to take good care of you while you're here," he said, giving me a wink.

The next half hour was spent driving through what looked to be some of the darker parts of Chicago. I had been there a few times on business, and didn't remember any theaters being in this part of town. Eventually, we exited the rough-looking city streets and, after driving a few minutes through what appeared to be a more residential area, turned into a gated facility that resembled some sort of country club.

Paul entered a number on a keypad and the gates began to swing open. He drove down a long drive, where a valet was waiting to take the auto. Again, Paul had to enter a number on a keypad to gain entrance to the building, and by now I had a twinge of excitement in my stomach. I had to wonder exactly what kind of a show would be on display in a place with so much security. I guessed that it was some sort of a swinger's club.

Once inside, I was almost surprised that we didn't find the place littered with naked bodies engaged in steamy sex. What we walked into was a beautifully decorated lobby that would rival even the nicest of hotels. Paul sauntered over to a man dressed in a tuxedo, who, in turn, then directed another man to usher us to our seats.

We were shown into a semi-private booth which had a back and two side walls. The front was completely open and looked out to a stage shielded by large black curtains. As I looked around the theater, this seemed to be the way all of the seating was arranged. I quickly surmised that this was to allow the patrons to enjoy each other while they enjoyed the show.

Inside the booth we found a single overstuffed couch that was plenty large enough to accommodate the four of us. I sat down, with Tiffany dropping beside me, and then Paul took a seat on the far end. Kelly, however, kneeled and then came to rest with her back against the couch and half-leaning on Paul's leg.

Tiffany gave me a questioning look and I shrugged my shoulders, although by now I had guessed that this was not just a swinger's club, but something a little darker. "Aren't you going to sit up here?" the naive girl questioned.

Paul cleared his throat and then flatly stated, "Submissives aren't allowed to sit on the furniture; Only doms and their guests."

Again Tiffany gave me a look and then it suddenly dawned on her what was taking place. "You mean this is an S&M club?" she questioned Paul, the surprise evident in her voice.

He nodded his head, chuckling a bit, then said, "Probably the nicest one in Chicago. We are very fortunate to have been asked to be members."

Paul went on, laying out the 'basics' for us concerning the rules and operation of the club. He told us that there was a show, like the one we were about to see, each Friday evening. Also, there were private 'play rooms' that members could use, as well as a large communal area where mingling, and open, spontaneous displays took place. "We can look around a bit after the show, if you want," he said as the entire theater began to grow dark.

A few seconds after the place went pitch black, bright lights lit up the stage. The curtains parted and two men, dressed in black leather pants and hoods, escorted a naked young woman onto the stage. They walked her to a large wooden frame that looked like a huge letter 'X' and secured her to it with chains. Her back was facing the audience and each of her hands and feet were attached to the opposite corners of the frame.

Tiffany wiggled a bit closer to me and put her hand on my leg, just above the knee. I could tell that she was a little tense, so I put my arm around her and quietly asked if she was all right. She just nodded her head silently, never taking her eyes off the stage. I had heard about places like this, but never dreamed that I'd find myself in one of them. I was fairly certain, though, that by the end of the evening I'd have a pretty good idea of how deep Tiffany's dominating tendencies were.

My only hope was that Tiffany wasn't going to get any bright ideas about trying to dominate me. I certainly wasn't a submissive, and I knew it could be considerably awkward and straining on our relationship if she tried. On the other hand, I also knew that we could have some wild times together if we could find someone willing to submit to both of us. Of course, there was always the possibility that she would be totally turned off by the whole thing, but I didn't think so.

Paul leaned over and whispered, "This show should be quite tame compared to some we've seen," just as a man appeared on the stage. He was dressed from head to toe in black, and wore a pair of dark sunglasses. He walked up to the woman on the frame, and you could tell that he was talking to her, but we couldn't hear anything he said. And, judging from what I'd seen of the layout earlier, I don't expect anyone else in the audience could have either.

Finishing his speech, the guy stepped back and admired the woman's naked form. One of his hands had been gently rubbing her bottom while he talked to her, and his fingers trailed off it as he stepped toward a table situated a few feet away. Once there, he surveyed the contents and selected his tool of torment. It was a black riding crop, much like the one some of us had used on Kelly that day on the mountain.

Already my heart had quickened, and the guy hadn't even landed a blow yet. I'm sure that Tiffany was the same way, her grip tightening on my leg. We watched earnestly as, over the course of the next several minutes, the man artfully swatted at the slave's backside and upper legs. The woman's hind-end quickly became covered with bright red patches where the crop had impacted her skin, but she didn't make sound. As he finished though, her head jerked visibly from the sting of the last four or five blows.

Tiffany's fingers were now clenched on my leg and she was transfixed by what she was witnessing. My initial astonishment was gone and I was really beginning to enjoy the show, hoping the same was true for her. I glanced at Paul and he was sitting back, relaxed, with an almost 'ho-hum' look about him. Kelly was still curled at his feet, and seemed quite content, with her head resting on his thigh. I had to wonder if she had been on that stage or not, and made a mental note to ask Paul about it later.

By now, the two hooded guys were back on the stage. After some preparation, the 'X' frame, girl still attached, lifted upwards and rotated 180 degrees. This left the female upside down with her back remaining toward the spectators. The 'hoods' disappeared and the man again went to work on the girl's ass with his riding crop. He landed eight or ten blows with the tool and then stepped forward to admire his work, close up.

The man ran his hand over the sub's reddened bottom, and then let it glide between her upturned thighs. His hand rubbed slowly over the woman's crotch for a few moments and then he stepped back again. He returned to the implement table and, after some thought, chose a new punishment device. This one had a handle that was about eighteen inches long, with several strips of what appeared to leather hanging from the end. These strips must've been at least three feet in length, and looked to be soft and flexible.

He waved the 'Cat-O-Nine', as I found out it was called, menacingly about for a moment and then struck the helpless victim squarely on her backside. There was a much louder, and longer, sound as the strips contacted her body. Instead of the quick 'smack' of the crop, there was a deeper 'whoosh' culminating with individualized, yet nearly simultaneous impacts that rang through the auditorium.

Another strike from the tool brought a sharp gasp from the woman. And then another blow was landed, causing her to writhe against her bonds. The dom paused and then spoke to the girl. "Do you want me to whip your pussy?" he asked.

I saw the girl's head move, almost imperceptibly, but didn't hear a sound. He asked again, with more force, "Do you want me to whip your pussy, slave?" And after a pause he added, "What's that... I can't hear you, slave... I'll ask you once more; Do you want me to whip your pussy?"

"Yes Master, please," the bound woman meekly replied.

"Yes Master, what?" the man taunted.

"Yes, Master. Please whip my pussy," the girl blurted.

The man teasingly flopped the tails of the device between her legs a few times, dragging them over her exposed cunt each time. "I'm thinking about ten strokes should do," he mused, then instructed, "Count them out for me, slave." And, without any further warning, he reared back, bringing the whip crashing down between the sub's legs.

"One," came the victim's voice. Another swing of the 'Cat' and she whined, "Two."

This continued until she reached the count of five. Then her tormenter paused to once more admire his handiwork. As his fingers roamed over her inner thighs, now becoming as crimson as her behind, I looked over at Tiffany. She was staring intently at the scene on the stage with a lusty twinkle in her eye that I hadn't seen for a while.

'Whoosh-Smack', and the slave called out, "Six," in a cracked voice.

The sounds drew my attention back to the stage just in time to watch the man deliver the seventh blow. "Uhhhh... Seven," the woman cried, "UhOww... Eight."

Another, harder, slap from the whip made her strain in the chains and whine with the sting, "Ohuhhh... Nu-nine." There was a very brief pause and then the instrument bit her crotch a final time. "Uhhh, hu-huhhh..." the slave whimpered.

"No, that's not correct, my dear. Try again," the master admonished.

"Oh-hohh... t-TEN!" the woman finally howled.

"That's my good girl," the man approved, running his hand up and down the female's inner thighs and then patting her cunt. The guy turned to face the audience and opened his arms wide in conclusion of his performance.

Applause broke out and he bowed at the waist, never giving any acknowledgment to his submissive partner. He bowed once more and then exited the stage, leaving his whip on the table from where he'd gotten it. As he exited, the 'hoods' returned and rotated the frame, returning the girl to her original, upright position.

The curtains closed across the stage, and I assumed the show was over. I turned to Paul and said, "That was certainly interesting."

"It was a good warm-up," he replied, adding, "The second act will be even better."

"Second act?" Tiffany asked with a scratchy voice.

"Yes. There are usually three acts to each show," Paul explained, "Unless they are special performances, and then you just never know." After a moment, he asked, "Would you guys like a drink?"

Tiffany and I both nodded and Paul picked up a phone on a small table at his end of the couch. He placed the order and hung up, then began petting Kelly's head. "We have seen some really wild things done at these shows," he confessed. "Most of them are very similar to what we're seeing tonight, but there have been some that..." He paused as if deciding whether to tell us or not, then went on, "Well, let's just say they wouldn't be for the weak of heart."

Kelly never said a word. She simply sat there like some kind of pet, soaking up whatever attention she was given. Again, Paul's voice rang out, "I'm sorry my darling. Since this is a special occasion, I suppose you are allowed to converse with us." And then he grabbed her hair and turned her face toward his, adding, "Provided you continue to be a good girl."

"Sorry; It's become her habit to follow the rules very well when we come here," Paul explained. "We usually aren't this way at home, unless we have special guests."

"Did you like the first act?" Kelly questioned Tiffany. The blonde nodded that she had and Kelly proceeded, "I'll show you some of our toys when we get home tonight."

"Okay," Tiff replied, her hand moving up my leg a little, toward my crotch. "So you guys come here a lot, then?" she inquired.

"Oh, yes. We are here almost every Friday night, at least for the show," Kelly beamed in response.

There was a knock on the door, and then it opened. A waiter came in with a tray that held our drinks. He served them to us, Paul gave him a tip, and he disappeared. I was still a little flabbergasted by the whole spectacle and quickly took a long drink from my hi-ball. This was a whole new experience for me, as it was for Tiffany. I was truly enjoying the event, but it was a good deal more than I had expected.

The lights began to go down and Paul said, "Here we go; Act two."

Again, the auditorium grew dark as night, and then the stage was flooded with light. The curtain parted and there was the girl, still chained to the 'X' frame. But now she was facing the audience and a blindfold covered her eyes. She was a very trim and petite thing, with small tits that barely swelled her chest, and what I call a 'Mohawk' trim job on her pubes. If I would have had to guess, she couldn't have been much older than Tiffany, if she were that old.

After a few moments, the stage lighting dimmed a little and the hooded men appeared, this time each carrying a large candelabra. They placed one on either side of the frame and lit the five large candles that they bore. The flames flickered hypnotically as the men departed, and another man replaced them on the stage. He was a different fellow than the first, but there was no mistaking that he was the 'Master' for this act.