Chicago Bound Ch. 02

Delving into her crevice, I found that she was indeed wet, and very much so. Pushing a finger deep into her, I asked, "Have you ever masturbated while thinking of Mistress Tiffany dominating you?"

Kelly closed her eyes and bit her lower lip, then murmured, "Mmm, Uh-huh."

My dick had begun to stiffen as I interrogated her, and I wanted more of her arousing delivery. "What was that?" I questioned, for my own benefit, but Tiffany's as well.

"Yes, Sir," she curtly answered.

"Yes, Sir... What?" I pushed.

"Yes, Sir, I have masturbated while thinking of Mistress Tiffany dominating me," she replied, seeming somewhat embarrassed.

I began wiggling my finger inside of her and stated, "You're going to have to say that a little louder. I don't think Mistress Tiffany could hear you," although I knew she could.

"Yes, Sir. I have mastur...." she started, but I interrupted.

"No. Louder," I enforced.

This time she repeated the whole phrase, much louder, drawing the attention of several people nearby. Kelly hung her head, humbled, but I'm sure quite excited at the same time.

I let another finger slip into her slimy, wet cooze and jammed the pair deep. "What would you like her to do to you, slave?" I probed.

"Anything Mistress wants to do, Sir," Kelly replied like a soldier in a line-up.

I knew that Kelly hadn't gotten off earlier, with the rest of us, and speculated that she was in need of release. Judging from her body language when I added a little thumb pressure over her clit, I guessed that if I continued toying with her I could make her cum rather easily. But, I decided that since Paul had given her to Tiffany for the weekend, I'd let her decide.

"I bet you'd like to cum, wouldn't you slave?" I tempted.

"Yes, Sir," she replied with a nod.

"Maybe you should ask permission," I said.

"May I cum, Sir?" Kelly quickly requested.

"You belong to Tiffany this weekend," I replied, "I think you need to ask her. But do it loudly, so she can hear you."

"May I cum, Mistress?" Kelly requested, loud enough that at least thirty people overheard.

"NO!" Tiffany barked, adding a more subtle explanation. "You will not be allowed to cum tonight. But if you please me tomorrow, I promise you will have an orgasm you won't soon forget." Then she told me, "Don't make her cum, Babe. Just let her sit down and think about it."

I pulled my fingers from the poor woman's soppy snatch and she let out a disparaged sigh. She stood there for a moment with a longing look on her face and then returned to her seat. As she sat down, I looked at Paul to see his reaction to this little scene. He was smiling widely in apparent contentedness of the treatment his wife was getting.

I picked up a napkin to wipe Kelly's womanly fluid from my fingers, but Tiffany stopped me. "Let her clean you up," she suggested. So, I presented my well-coated fingers to Kelly and she lovingly took my hand in hers. She slowly licked and sucked each of the two digits until they were completely free of her own nectar, then she dried them with her napkin.

While she was performing this duty, Tiffany made Paul promise not to get his wife off overnight. He agreed to her plan, but asked what he was supposed to do if he decided he needed a little more relief tonight. "Oh, don't worry," she touted, "The other three of us can have as much fun as we want."

"Speaking of fun," Paul began, "Would you like to go get a private room and have some fun with our pet? Or are you ready to head for home?"

"A room does sound inviting, but that was a long flight this afternoon," Tiffany answered. "I think I'm ready to get back to the house and get some rest."

"Yeah, me too. I'm pretty worn out," I seconded.

Paul motioned for our server and requested the check. While we were waiting for it to arrive, he leaned over and whispered something to Tiffany. She grinned with a devious look and I suspected that he was feeding her ideas for our Kelly. He started to move away, but then leaned close to her again. As he spoke to her, Tiffany's head nodded and she nearly broke out in laughter. I could only imagine the perils that she was plotting for the sub.

The tailed woman brought a small silver tray to the table that held our bill. Paul signed it and the woman picked up the tray, then smiled and said, "Happy bondings and enjoy your evening." She turned and strode away, her long tail flipping from side to side. Even if it wasn't bondage related, I thought the tail would be a cool accessory to see any woman walk around with.

We left the table, Tiffany picking up Kelly's leash again, and Paul led us out of the 'playground'. Traversing a couple more of the elegant corridors, we rounded a corner and entered another area resembling a lobby. "Let's go out the back," he called over his shoulder.

I was beginning to wonder about Kelly's clothing, which we had left in the theater booth. I assumed that we would return there so she could get dressed. But it was obvious that we were nowhere near that part of the building. I started to ask him about it, but before I could, Tiffany began speaking.

"Paul tells me that your clothing has been gathered by the staff and you can pick it up any time," she began. "Which means that you will be riding home as you are, my pet," she told Kelly.

"But Mistress, I..." Kelly began to stammer in protest, but Tiffany quickly cut her short.

"Hush up or you'll find yourself walking home naked," she threatened. "Besides, if you get dressed, how will I be able to do this in the car?" the blonde posed, slipping her hand between the slave's thighs. And from the look of surprise on Kelly's face, I would say my baby had also dipped a finger into the submissive's hole.

Kelly stood there for a moment with that astonished look, then meekly said, "I'm sorry Mistress. It's just that I've never had to do that before, and I'm afraid..."

She paused and Tiffany quizzed her, "Afraid of what, being seen?" Then Tiff went on, "Well, you might be. In fact, I hope you are. I'd be proud to have people know you're my pet."

"Really, Mistress?" Kelly beamed.

"Yes, you have a beautiful body..." she volleyed as she withdrew her hand from Kelly's crotch. She sucked one of her fingers into her mouth, removing it to finish her statement, "And you taste good too, my dear."

"Thank you, Mistress," Kelly replied contentedly.

"Come on, the car's here," Paul told us, and we headed for the door.

Kelly unabashedly bounced out the door and walked to the car in all of her naked splendor. Reaching the auto, she opened the rear door closest to her and motioned for Tiffany to get in. As my sweetheart took her seat, she informed Kelly that she needed to go around and open my door as well. I think she was just trying to parade her around as much as she could. But Kelly didn't hesitate and rounded the car to usher me inside.

Once we were all in the car, Tiffany remarked, "I wish we had a towel or something so our little slave girl doesn't leave a stain on your seat from her wet little pussy."

Quickly, Paul exited and went to the trunk. He returned with a small blanket and handed it over the seat to Tiffany. "Here, this should do the trick," he told her, then reseated himself behind the wheel. He waited for the females to get themselves situated and then drove away.

As we made our way back to their house, I noticed Paul smiling as he looked in the mirror. I turned to see what was so entertaining and found Tiffany fingering Kelly and sucking on her studded nipples. "So how long has Kelly had the piercings?" I questioned.

"Oh, about seven or eight months now," the driver replied. "It's kind of a funny story. Those pierced nips are how we ended up at that club."

"Really? How so?" I asked.

Paul launched into an explanation, "She decided she wanted to get it done, and of course I was all for it. We went to an upscale tattoo shop that did piercing, and this cute little Goth chick waited on us. Kelly and I both thought she was hot, and decided to see if we could hook up with her. As it turned out, she was a dominatrix, and a member of the club."

After stopping at a stop sign, checking for cross traffic and then moving on, he also moved on with his story. "Ever since our vacation with you guys, we had been playing with B&D a little more. Yvonne, the Goth chick, helped us really develop it. After a couple of months, she sponsored us into the club."

"Do you guys still see her?" I wanted to know.

"Not so much anymore. It's been well over a month now," he said, then smiled and added "I guess we've kind of outgrown her."

"Ohhh, Mistress. That feels so good," Kelly moaned, drawing my attention to the back seat again. Tiffany was still plunging a pair of fingers in and out of the nude Kelly, but now she was biting the swell of one of the woman's breasts. "Ohh, god, that hurts, Mistress," she whined. And when Tiffany lifted her head, the teeth marks were clearly evident on the sub's flesh, even in the darkened car.

"I don't want to spoil the mood or anything," Paul called out, "But it looks like things are heating up, and I just wanted to let you know that your slave has a 'safe word'."

"Safe word?" I queried.

"Yeah. Remember what Master Wolfe said about etiquette and pain?" he wondered.

"Yes. I remember," I nodded.

"Kelly can take quite a bit, and will diligently try to accept whatever you give her. She might whine, complain, or even cry out, but not want you to stop what you're doing. So it can be difficult to know when you've gone too far. Thus, the 'safe word'. If, at any time, she says 'white bread', you've gone beyond what she can handle and need to stop," Paul explained.

"Have you ever made her use it?" Tiffany asked.

"No, I haven't, but Yvonne did a couple of times," he answered. "But both times, our little trooper wanted to keep playing after a few minutes, though."

"You're such a good little slave. Aren't you my pet?" Tiffany doted, brushing her hand down the side of Kelly's face.

"Yes, Mistress," Kelly smugly replied.

"Let's see how good you want to be," Tiffany sadistically announced. "Pull over in that lot, Paul."

Paul wheeled the car into a nearly empty parking lot and Tiffany directed him to a parking spot, "Right there will be fine." He stopped the car and we were looking out onto the street from which we'd come. Tiffany commanded Kelly to get out and, hesitantly, the sub opened the door and exited the vehicle, Tiffany right behind her. Paul and I both got out, I'm certain with him wondering, as I was, what the little dom had in mind.

"Come on!" Tiffany growled, pulling at Kelly's leash. "Come up here and put your hands on the hood of the car," she demanded. "Now spread your feet... Wider... That's good." When she finished, Kelly's bare ass was pointed directly at the street, only a few feet away, in a semi spread-eagle stance.

"But Mistress..." Kelly complained, "What if someone comes by?"

"Hush up, you bad girl. That was a very naughty thing you did; letting me stick my fingers in you like that." Tiffany was really getting into character now. "You will be punished now."

"But Mistress, I thought that's what you wanted," the slave whined.

"But you were enjoying it too much, you little slut," Tiffany chastised.

"Mistress, please... Someone's gonna see," Kelly pleaded.

"Shut up! You will stand there until I say differently. Do you understand me?" Tiff grumbled like a displeased mother.

"Yes, Mistress," came the sheepish reply.

Tiffany walked over to me and began to fumble with my belt buckle. At first I thought she was trying to get in my pants, but then I realized she was only trying to get my belt off. Once she had it free of the loops, she doubled it over and turned back toward her victim. I think curiosity had simply gotten the better of her and she wanted to test the water, to get a better idea of how far she could push Kelly.

"I am going to spank you with this belt, slave," she menaced. "Count the blows out loud."

"Please, Mistr..." Kelly started to beg for mercy again, but the first delivery was already on its way. The belt landed squarely on Kelly's full buttocks with a loud slap. "Owww.... One," she called out. Another quick flip of Tiff's arm and, "Ohhh... Two."

"Louder, bitch," Tiffany griped as she swung her arm a third time.

'SMACK' The belt landed again and Kelly increased her volume, "Three." Again she tried to beg for sympathy but was interrupted by the belt, "Please Mistress. I... 'SMACK' Oww-ohhh... Fouruhh."

Two more whacks were brought down on Kelly's reddening ass and you could see her legs start trembling. Her voice was becoming more shrill with each slap of the leather. The seventh blow caused her knees to buckle slightly, but she regained her stance and called out, "Sssevuhhn."

My heart was pounding and my boner had returned, in full force. But the funny thing was, I didn't know which one I wanted to fuck more, Tiff or Kelly. I was totally turned on by the way my girl was handling her 'pet', but at the same time I wanted to feel the heat from Kelly's ass against my stomach as I fucked her from behind. It was a hell of a quandary, and one that would have to wait.

Just as Tiffany brought the belt crashing down on Kelly's butt again, a car turned the corner and drove right past us. "Uhhh-OWW... Mistress, please," Kelly pleaded. The car slowed at the next corner and turned left.

"How many was that, slave?" Tiffany questioned unforgivingly.

"Looks like they're coming around for another look," Paul observed.

"Oh God, Mistress, Pleassse. They're coming back," the sub whined.

"How many, slut?" Tiffany growled again.

"EIGHT, MISTRESS, EIGHT!" Kelly bellowed, almost crying.

"That's better, you can turn around now," Tiffany told her.

Just as she started to rotate her body, the car indeed did come around the corner again. It slowed to a crawl on the street, and then stopped directly in front of us. Kelly quickly halted her turn and flashed her back to the street again. As they stuck their heads out the windows, I could tell that the spectators were nothing more than a bunch of drunken college boys, and meant us no harm.

"Woo-hooo!" one of them yelled, "Let's see the rest of her!"

"Turn around slave," Tiffany calmly ordered.

"Please, no Mistress," Kelly begged.

"Turn around and show them your tits and pussy, or I'll invite them to come over here and spank you some more," Tiffany quietly seethed.

Hesitantly, Kelly turned her body until she was giving the rowdy carload a full view of her front side. The young men hooted and hollered their approval, while Kelly just hung her head, thoroughly humiliated.

After ogling the poor sub for a minute or two, shouting various crude remarks, the driver gunned the gas and they disappeared.

"I think we ought to be moving along," Paul remarked after the other car was out of sight.

"Yeah, I agree," Tiffany replied, "Either get me home or fuck me right here."

Apparently the thrill of dominating Kelly was having profound effects on my girl. Of course, she never had been as bashful about public exposure as most people, at least not since I'd met her. But having sex in an empty parking lot at midnight in Chicago is probably not the best idea. So, I too, agreed that it was time to leave.

Before we got back in the vehicle, Tiffany shoved her hand in Kelly's cunt once again. A few seconds later, she pulled it away, commenting, "Damn... That really got her flowing." And then to further humiliate the woman, she pulled on her leash, asking, "You really liked that, didn't you slut?"

Kelly shook her head 'no', but didn't say a word. Tiffany jerked the leash rather hard and demanded, "Tell the truth right now or we'll do it all over again!"

"Yes Mistress, I did enjoy it," Kelly mumbled.

Tiffany led her to the car and within a minute or two we were back on the road. About ten minutes later, we pulled into Paul and Kelly's driveway. As we started to get out, I noticed that one of their neighbors was conducting a party in his back yard, which was still going strong. There was no way that Kelly was going to make it to the door without being seen. I had to wonder what Tiffany was going to do.

I decided that I didn't want to cause problems for our hosts, and started to tell Tiffany that we couldn't jeopardize their home's security. When I turned to convey my concerns, Tiff was already draping the blanket over Kelly's shoulders, pulling it around her. "If anyone asks, just say that she became ill and vomited on her clothes," the intuitive little blonde smiled.

We quickly exited the car and headed for the house. Tiffany walked with one arm around Kelly, her other hand still holding the leash, but camouflaged by the blanket. As fate would have it, Paul's neighbor did notice us. Wandering over, he drunkenly questioned if everything was okay. Paul gave him the vomit story and the guy bought it, hook, line, and sinker. Once safely inside, the three of us broke into laughter and I even noticed a wide smile creep across Kelly's face.

Tiffany gave the blanket a flip, letting it fall to the floor. Kelly's plump backside was still streaked red from the belting she'd received. My girl embraced her, mashing her lips to the brunette's. They kissed passionately for a few moments while Mistress Tiffany let her hands slide lower and lower, over the full roundness of her slave's bottom.

Ending the kiss, Tiff stepped back and drew her sun dress up and over her head, revealing her tight, young nakedness to us again. Then, she moved forward and the pair wrapped their arms around each other, bringing their bodies together. Two pairs of lips and boobs pressed to one another, their tongues chasing back and forth in an extremely hot exhibition of pure lust.

Paul and I watched the pair for a moment and then looked at each other, both of us with a 'what the hell are we waiting for?' expression. We began to peel out of our clothes and soon joined the females in the freedom of our birthday suits. By the time we finished, the two women had broken their kiss and were peering into each other's eyes.

"You've been a very good girl this evening," Tiffany began, then asked again, "Did you enjoy having your ass spanked out in public?"

Sheepishly, Kelly replied, "Yes Ma'am, it felt wonderful." And then after a brief pause, she spoke again, "Mistress..."

"What is it my pet?" Tiffany returned.

"May I go to the bathroom?" she requested, "I really need to pee."

I don't think it was until then that I understood just how submissive Kelly had become. It's funny how the simplest of things often bring us the greatest of realizations. I mean, Kelly had submitted to some strange, and painful things that evening, but that was all part of the 'game'. For her to ask permission to use her own bathroom; that was a telling signal that she was totally committed to her role of servitude.

"How bad do you need to go?" Tiffany taunted the woman.

"Very bad, Mistress," came the reply.

"Well, I don't know...." my little sadist mused, taking a step back to run her hand down the sub's abdomen. "Do you really have to go?" she questioned, pressing inward just above Kelly's pubic mound.

"Uhhh... Oh-God.. Huhhh... Yes, Mistress," Kelly moaned under the torment, her face turning to a deep grimace as she struggled to answer.

"Maybe I should make you piss yourself so we can watch," the Mistress teased.

"Uhhh... Ple-e-ease Mistress," the sub whined, beginning to dance around in an effort to contain her urine.

"Well, I guess I wouldn't want you to make a mess on Paul's carpet, so go on," Tiffany relented.

Kelly bolted from the room and Tiffany turned her attention to Paul and me. Stepping between us, she grabbed a pecker in each hand and started slowly stroking us. She giggled and said, "I hope she hurries, I gotta go too."