On the Road Again Ch. 02

"Please Mistress," I repeated over and over. "I need to cum. May I please cum?"

I imagined her smiling at me as she looked down over Mary's body writhing on her strap-on. Finally Victoria relented. Oh she didn't just tell me to cum. That would be too easy. Instead she said, "Ten." I knew what that meant based on our experience last night. Each number was accompanied by two, what I can only assume were savage thrusts, based on Mary's reaction.

"Nine," she said. This time Mary begged for permission to cum, but none was given.

For all the world to see, it seemed like Mary was Victoria's submissive. Like me, she must have been struggling not to cum. Like me, she must have wanted to be a good girl. Maybe Victoria threatened to punish her for climaxing too soon.

"Eight." I let out a shriek as Mary's chin slid across my clit.

The rest was a blur. Much like last night, I began having an out of body experience where I was floating above my body and watching the carnal scene like a live porno. My own struggle to hold back my orgasm subsided, although my body knew its release was imminent. I was on the precipice, but waiting for my Mistress to grant her approval. It was an amazing feeling, one I still didn't understand, but I wasn't worrying about it. With my other partners, I would have to actively think of fantasies to try and cum, mostly without success. But with Victoria, I just had to let her play my body like a fine instrument and my orgasm would flow on her command.

You won't be surprised to know we both came simultaneously and at the proper time when the countdown reached zero. While I was wrecked and happy to be lying down, Mary seemed invigorated and got up, thanking Victoria (not Mistress) for the great fuck. "I have to get back to work babe," she said. "Call me next time you need to break in a new girl."

I heard the door open and shut moments later. In my mind, Mary had walked in, raised her skirt, bent over to eat my pussy, got screwed, stood up while pulling down her skirt and left. A fine lunch break, to be sure, but I had more important things on my mind. I opened my mouth to ask Victoria what was next, but I felt the head of her strap-on being pushed into my mouth. I have sucked enough cock to know what she wanted. Mary's flavor coated the shaft and I enjoyed the treat. She tasted different from Victoria. Not better, but different. I anticipated Victoria wanted me to clean her toy and I did the best I could, although she pulled it out of my mouth just 30 seconds or so later.

"Please fuck me, Mistress," I told her without feeling embarrassed.

"I have a client coming in," she announced. "We have to get you cleaned up and out of here."

Of course I hoped she was going to keep me for the afternoon. When she added, "If you're interested, I have tonight free," I told her of course I was interested. She took off my blindfold and then released me from my bonds.

"Just put your dress on and go to the bathroom down the hall. I'll tidy up here," she told me.

I felt like a dirty slut without my bra or panties, even if both were kinky in their own right. I found the bathroom and did my business. I was sure Victoria was going to make me walk around in those terrible (or wonderful) panties while she worked this afternoon. Since I'd just cum, hopefully it would be a little easier. When I got back to Victoria's office, however, both garments were missing from the couch and Victoria was holding what looked like a leather belt.

"Lift your dress, pet," she said with a surprising amount of warmth. I did as she asked.

She then handed me the belt. "Hold this," she said. I got to look at it and saw that the belt also had a strap that I assumed went between the legs. It obviously wasn't a locking panty like I had been wearing, but it was similar and I saw a locking mechanism on the back, but there was no teasing nub in the front. Thank God for small favors, I thought. Perhaps I thought too soon.

"Bend over the back of the couch," my Mistress commanded. I obeyed.

"If you want to serve me tonight, I want you at least as horny as you were this morning," she told me with pride. I kind of smiled, although I was a bit worried as well. I guess my relief on Mary's face would be short lived. Then I felt her rubbing my ass.

"I remember you told me you had never had anything in your ass before," she said remembering our conversation yesterday. I then felt a cool gel drip between my ass cheeks.

"Don't worry. This is a small plug to get you started," she continued as if that would be reassuring.

Maybe it was small, but it felt big to me.

"Push against it and you'll open up," she instructed. I tried, she was insistent pushing firmly, and pop, in it went. I grunted. "Perfect," she added as my ass snapped around the smaller stem.

I wiggled my ass trying to get accustomed to the invader. I also wanted to give Victoria a bit of a show. She responded by putting her hand between my legs and rubbing my pussy. I moaned.

"Don't worry," she said, this time as more of a taunt. "I didn't forget about your slut hole."

"My what hole?" I thought in a panic. I stopped wiggling and Victoria's fingers spread my pussy lips. I thought maybe she was going to put in another remote vibrator. But instead I felt a cold metal ball pushing inside my pussy. Then a second one joined it. "Hold still," she said. I didn't dare move.

Next she took the belt that I had dropped on the couch. She wrapped it around my waist and then slid the strap as I had anticipated between my legs and secured it.

"This serves two purposes," she told me. "First it holds those balls and the plug in. Second, it acts as a chastity belt so you can't rub your clit."

I didn't think of it in those terms, but in a way that was worse than the panties because I probably could have gotten myself off when I was wearing them by rubbing myself against something hard. This belt was very firm and strapped very tightly against me so I probably couldn't get any friction against my happy spot. At least I wouldn't be rubbing my clit with every step.

"Stand up and pull your dress down," Victoria commanded. As I did, I took a step to steady myself and I felt the balls move in my pussy. I looked at Victoria as if to say, "Are they supposed to do that?" Her smile told me they were. I straightened my dress and I could feel my nipples rubbing against the course material. I could tell that, even without the bra, my nipples were going to stay hard.

"You said you wanted to visit the Art Institute," Victoria pronounced. "I want you to walk down there and enjoy the exhibits. You won't draw attention to yourself if you need to stand in place for a while to avoid orgasming. I might have a friend or two keeping tabs on you, so don't think you can sneak into a corner and make yourself cum."

I have to admit, Victoria was a planner. First my shopping trip, then the rendezvous in her office and now this. "Of course Mistress," I replied. "I won't cum without permission."

I said the words I knew she wanted me to say, but I didn't know if they were 100% true. I'd never been plugged or worn balls in my pussy. I was sure they would tease me like the leather panties had, but I hoped I could handle them.

Almost as an afterthought, Victoria went back to her desk, opened the drawer and pulled out a short black strap. She walked back to me and told me to lift my hair before putting the strap around my neck and clipping it shut. It was very snug, but not uncomfortable.

Victoria then spun me around, pulled me into a tight embrace and gave me a very passionate kiss.

"That choker will let anybody in the lifestyle know what you are. Do not remove it. If you can handle this task, I will give you a night to remember tonight," she promised. "Now get out of here. Use the left door as my client will be here any moment. I will text you instructions later."

And just like that I was dismissed and Victoria went back into therapist mode. As I walked out of the second office into the hallway, I saw a man walking into the main office. He glanced at me and I wondered if he thought I was just a normal patient. As I took two steps toward the elevator the balls shifted and reminded me that nothing since the bar last night was normal. I took a couple of full steps, something I didn't dare do with the panties on and I found I could handle the motion of the balls, but that the plug rubbed me in, shall we say, a very nice way.

As I exited the building out onto the sidewalk, I determined that full steps turned me on from the plug and that shorter steps made the balls dance in a pleasurable way. They also moved haphazardly with full steps. Basically I couldn't predict when they might hit a nerve and send a pleasure shock through me. I headed up Adams Street toward the Art Institute. The hustle and bustle of the city meant people were around me, but my sluttiness was hidden, except for the choker. And that was a turn-on. I did wonder if anybody noticed it. Some people, both men and women, looked at me, but I couldn't tell if they suspected something or just thought I was attractive. It didn't matter. Each step I took reminded me of Victoria and my nipples rubbing against my dress drove my arousal higher.

I made it to the Art Institute without incident, other than a growing need to climax again. It wasn't as immediate as the panties and bra had dictated, but I was definitely aroused. I looked around to see if I could identify one of Victoria's spies, but nobody seemed to be following me. I set myself to the task of wandering the wonderful exhibits, something I really wanted to do. But the growing need between my legs began to make that more difficult. While my build to near peak arousal was slower this time, it was nonetheless strong and distracting. As Mistress had predicted, within an hour or so, I had to stop to admire a picture without moving to avoid orgasming. I imagined her spies watching me and knowing whenever I stopped for a minute or two knowing the reason.

Soon just walking from one room to another was enough to put me on edge. I kept looking at my phone to see what time it was and to wait for Mistress' message giving me instructions. I didn't know how many clients she had this afternoon. For all I knew, she had some tonight as well. I knew the Art Institute was open until 8 on Thursdays. I prayed she didn't make me wait that long. Of course she could send me instructions to meet her just about anywhere and at any time. I then began to worry about being able to go to the bathroom. I didn't need to go yet, but if she made me wait until 8, I was going to get very uncomfortable.

Fortunately, about 5:15 I got a text from her. "Meet me on the Art Institute front steps in 15 minutes or head back to your hotel and go home tomorrow."

I took a deep breath and started heading for the exit. Slowly. I had the anticipation of seeing Victoria to add to the dual action of the balls and plug, and while I had been maintaining my level of arousal, I didn't want to risk moving too quickly. I also didn't want to move too slowly. I was quite a way from the front entrance and the museum was busy, so I figured it might take a full 15 minutes to get out to the street.

As I exited the building, I saw Victoria standing at the bottom of the entrance steps. She was looking at her watch. I had not checked the time so I wasn't sure if I made her deadline. I hurried down the stairs faster than I should have, resulting in me having to freeze and bend forward a bit when I reached her to prevent myself from cumming. I figured she would appreciate that.

"You're a minute late," she told me. "But you're so damn cute, I think I can let it slide this time."

I didn't want to be thought of as cute. I wanted her to think I was sexy. But I also didn't want to think about her giving up on me because I was a minute late.

"Thank you, Mistress," I said, still struggling not to move.

"Stand up straight, pet," she told me. I slowly did.

"It looks like the balls have had their desired effect," she said proudly. "If you serve me well tonight, I will give you the relief you desire. As I recall, you wanted me to fuck you."

"Yes, Mistress," I replied. "That would be amazing." I answered with a firm voice and a confident tone. It was then I remembered we were on a street corner as I realized people were passing us and I'm sure some people heard our conversation as a couple walking by both turned to look at me. I weakly smiled.

"My condo is not far from here," Victoria said. "As I recall from our conversation yesterday, most of your partners left you to finish for yourself and your best partner only got you off twice."

I couldn't believe she was sharing my intimate secrets in public.

"Tonight we will set a new standard for making your slut hole gush," she added.

Now I was getting embarrassed. She told me to pick a number between three and five. Jokingly I picked five trying to call her bluff. Even the time I came twice was a struggle to reach number two. Victoria stopped a man who was about to cross the street and asked to borrow a coin. I think he had heard our conversation because he handed over a quarter without asking why.

"Heads means five," she said. "Tails mean we multiply by two."

We both watched as she flipped the quarter, caught it in her right hand and then flipped it over against the back of her left hand. She held her hand over the coin and then shielded the coin so I couldn't see it but the man could. They both smiled and then she handed the quarter back to him.

"I don't suppose you need any help?" the man asked.

"Not tonight, but thanks for volunteering," Victoria replied. Then he looked at me.

"Have fun," he said before turning and crossing the street.

"What's the verdict?" I asked.

"Let's just say when I send you back to your hotel, you're going to be tired, sore and worn out," was her smiling reply.

It must have been tails, I mused.

Victoria put her arm around the small of my back and led me South on Michigan Avenue. If you saw us, we looked like a normal lesbian couple, although I felt her hand was showing possession. We walked maybe six blocks until we crossed the street in front of a high rise condo building where a doorman opened the door and greeted Victoria by name. They expressed pleasantries and she informed him that she would be having dinner delivered and to let them up. He said he would and we went inside.

Once we were in the elevator, Victoria went into Mistress mode pinning my wrists against the wall and kissing me aggressively. She then backed off but continued to hold my wrist firmly against the wall. I looked over her shoulder and saw a security camera.

"Don't worry about that. They've seen much worse. You're going to be my good slut slave tonight, aren't you?" she said firmly.

"Yes, Mistress," I replied. I wanted to add that as long as she made me cum, I would do anything she asked. But she already knew that and after all, had promised me more orgasms than I had ever experienced in a single night. I must admit I was a bit concerned with what she would do in the privacy of her home, but I also knew I needed this. If I had gone back to the hotel, I could have gotten myself off in a matter of minutes, or seconds, but I'd always have wondered what I had missed.

The elevator doors opened and she led me down the hallway, only now her hand was under my dress and she was playing with the plug. I didn't think I was ready to be fucked in the ass, but I also knew what I thought on the subject didn't matter. I just hoped she would let me cum quickly. We walked to the end of the hall and she pulled out a key.

"Take your dress off," she commanded. I knew we would be standing here until I complied. I looked up to see if there was another security camera. The answer was yes. Well, they already had footage of us in the elevator so I guess it didn't matter. I pulled up my dress and handed it to Victoria. She said nothing, but her smile told me she was pleased. At least she didn't take the belt off and show off my wet pussy. She unlocked the door and ushered me inside.

Her condo was absolutely neat and tidy. I expected nothing less from what I knew about her. It was also tastefully appointed. I kind of thought it might have more of a dungeon motif, but it was well fashioned and modernly designed. Because she was on a corner, she had views both East over the lake and North up Michigan Avenue. I hated to think how much more expensive this condo would be compared to mine in St. Louis. Her HOA was probably more than my mortgage.

After setting down her bag, Victoria came over to me and said, "Let's get that belt off you and the plug out."

I was relieved she wanted to remove the plug. She didn't mention the balls, but I assumed she meant them too. She removed the strap and I felt odd without it. In a way, it represented safety as my lady parts were protected. She wiggled the plug a bit and then tugged. I would later learn how easy such a small plug was to insert and remove, although at that moment, it felt very large as I had to stretch to let it pop free. Victoria handed it to me and told me to hold it. That seemed strange.

She then knelt down and told me to lift my right foot. She took off my shoe and then rolled down my stockings. She then repeated the process on my left leg. I was left holding the smelly plug, still wearing the choker symbolizing my submission to Victoria and still stuffed with the metal balls.

"Go into the bathroom and wash the plug," she instructed. "Don't let the balls slide out or I'll have to punish you."

I took a couple full steps toward what looked like a hallway where I assumed the bathroom was located. As I did, I felt the balls shift. Instinctively I clamped down with my pussy muscles, but my pussy was too wet and I basically shot the lower one out. The sound of it bouncing on the wood floor was something I will never forget. It wasn't that loud, but to me it was deafening.

"Somebody is wet," Mistress said with a snicker. "You better take out the other one and wash both with the plug, you dumb slut."

Victoria didn't seem upset. I think she was pretending. She was probably thankful that I gave her an excuse to punish me, not that she needed one. I resumed heading toward the bathroom while Victoria took out her cell phone and began a call. I couldn't hear who she was talking to as I washed the toys. She probably was placing a dinner order, although in my brain fog of arousal, I fantasized about her calling Mary or a different friend to come over tonight and use me. The urge to masturbate was very strong, but I resisted. I'd held back this long. I wanted to please Victoria and not cum until she gave me permission. When I returned to the living room, Victoria was gone. I looked in the kitchen, but she was not there either. I just went to the window to admire the view. I wasn't concerned with anybody seeing me. I didn't have long to wait.

I knew Victoria entered the room from the sound of her heels clicking on the floor. Since she had taken off my shoes, my movements were quiet. I turned to look at her and she had shed her professional clothes and was now wearing, well, I guess they were still professional but now her profession was dominatrix. She wore a black corset that pushed her exposed breasts up, tightened her already small waist and left her pussy exposed. My mouth watered in anticipation of getting a second chance at making her cum with my tongue. This time we wouldn't need to hurry. She was also wearing leather thigh high boots with what looked like a four-inch heel. I'm pretty confident she saw the look of lust on my face.

"Come over behind the couch, little one," she told me as she walked behind the couch that was positioned opposite the front door. I quickly followed her. "Bend over the back," she added when I got there. I quickly did, feeling very exposed. She ran a finger up the length of my slit. I doubt she was surprised when it came back wet.