Decision Tree Ð Chapter 04 By Tappy McWidestance
I was on pins and needles wondering what my punishment would be. I had cum without permission, although I had been setup to fail. I knew Sir had done that just as an excuse to further my training with some negative reinforcement. I wondered if it would really be that negative though. I had read a lot about spanking and it seems like many women find it helps get them into subspace where they can really let themselves go. I always felt only playing with James on Fridays was punishment. If a spanking helped arouse me that would hardly be a bad thing.
As I told you before, James had setup an Amazon wish list where he put toys he wanted me to buy. The strange thing was we hadn't used any of them yet. He had me buy four leather cuffs, a Hitachi Wand (I was dying to try that one out) a better webcam, nipple clamps, a flogger and a riding crop. I assumed he had my training planned well in advance and that I would soon be ordered to cuff myself and then somehow hit myself with the flogger or crop. I anticipated that he wanted to watch as well with a better picture than the webcam on my laptop provided. I was surprised when I got an email from him late in the day on Wednesday with different instructions.
I was to go to a specific adult bookstore on Washington Street just west of the Loop where I worked. It wasn't far, but it screwed up my taking the train home that night. I suppose I could grab an Uber, although I would have to find someplace respectable nearby to give as my destination. At the store I was to buy a paddle. It was to be leather covered, firm and have some weight to it. The instructions said to pick up several paddles for comparison and I would understand what he meant by having some weight. I was also to buy an anal training kit and a collar. He told me not to spend much on the collar, as it was not meant to show commitment but was more for play at this point. He told me he would purchase a better collar himself if and when he chose to collar me. He told me to take a picture of what I bought and to send it to him. He also told me to be online at 9pm.
Walking into the store by myself was a little nerve wracking. The place wasn't a seedy dump, but it wasn't an upscale boutique either. I didn't see any other women. That made me nervous and more than a little embarrassed. Of course the clerk asked if I needed help. I doubt he asked the guys that. But I am sure he doesn't get many beautiful women in tailored business suits walking through the door, so I should have expected a bit of attention. I tried to sound calm as I politely told him I was just browsing. I didn't want him to know I had a shopping list. He too was polite and told me if I needed anything (yes he stressed the word anything) to let him know. I just nodded and started looking for the paddles.
They didn't have a big selection, but I quickly understood what Sir meant by picking one with some weight. They had long narrow paddles that were very heavy, small round ones that looked like ping pong paddles and weight about as much and kind of medium sized ones. I hit my hand with both the small and medium paddles. The small paddle made a big noise, but didn't really sting. The medium paddle had a less impressive thud sound, but hurt much more. I couldn't really use the large paddle to hit my hand and I didn't want to ask for a volunteer to use it to hit my butt, but looking at the construction of it, I am sure the added weight would mean a much higher pain factor. I decided Sir meant for me to buy the medium paddle. It was big enough to sting, but not so big that I couldn't use it on myself if that was what he had in mind. Looking up after I made my decision, I discovered I had a small audience that had been watching. Again, I suppose that was to be expected. I only hoped they would keep their distance. Or did I.
The collars were in the same section. Again they didn't have much of a selection. This store seemed to focus on videos. I did notice some guys going into a back hallway so I deduced they also had video booths. My pussy was wet from hitting my palm with the paddle and from touching the leather collars and imagining them around my neck, but I didn't dare go into a private area by myself. I quickly chose a one-inch thick collar with a d-ring in front. It was faux leather and cheaply constructed, but inexpensive and I figured it would do for now.
Surprisingly they had a better selection of vibrators, dildos and anal plugs. It was almost a disappointment because I was a bit bewildered by the selection. Since I didn't have a lot of choice on the paddle and collar, it was easy to pick one. But unfortunately, as my husband always complains, I need to do my research and it takes me a long time to choose something when we are shopping. In this context, that meant picking up each plug package and most of the vibrators too. Sir didn't say I couldn't get a special treat for myself. I could feel the eyes of the men in the store watching me. I don't know why I found that humiliating since they were obviously as perverted as me. Well maybe not as perverted, but certainly they were no better than me. I really wasn't sure what Sir wanted me to buy and I almost convinced myself to ask for help (I was trying to avoid that at all cost) but then I spotted a combo product in a clamshell plastic package on the bottom shelf that was almost hidden. Before I picked it up I knew it was what Sir and sent me to acquire.
The package contained three different butt plus from pretty tiny (that's no big deal) to medium (that's going to hurt) to large (what the fuck? That's not going in my ass) sizes. It looked like they were rubber or some kind of extruded plastic. I had been looking at glass ones. They looked prettier and I figured would clean easier, but the words "anal training kit" on a piece of paper inside the plastic tipped me off that this was the product for me. I thought about buying one of the pretty glass ones too, but I decided to wait for another day. If the training kit was a disaster, I didn't want to have wasted money on a high quality plug too. My face was beet red by the time I took my collection to the counter to pay. I wanted nothing more than to get out of there in a hurry and get home. The clerk asked for my ID since I paid with my debit card. I was worried about him seeing my address, but I handed him my driver's license anyway so I could get moving.
Fortunately it didn't take long for an Uber driver to pick me up. My new toys were in a non-descript bag and I had the driver pick me up from a restaurant across the street. My ruse fooled him, although all the way back to the apartment I wanted to pull out my collar and the paddle and feel their texture. I wanted to know what the collar felt like around my neck and I wanted to know what the paddle felt like against my soft skin. But I couldn't indulge myself. I just let the package sit next to me on the back seat. I kept calling to me to open it, but all I could do was slowly and quietly rub my thighs together. As we got closer and closer to my place, I got more and more excited. I couldn't wait for John to leave for work so I could get online.
At 9pm sharp I logged into the chat room. I was dressed, as I had learned to be, ready in case Sir wanted me to turn on my camera. I was wearing a garter belt, stockings and stiletto heels. I wasn't wearing anything else and my nipples, as usual, were rock hard and aching to be touched. I hoped he would let me. Oh, and yes I was wet. I hoped he would let me touch my pussy too.
I could tell as soon as we connected by cam that although he told me I needed to be punished for cumming without permission, he was really pleased with how it happened. I wished he would stop using the voice manipulation so I could hear his real voice and his tone, but I sensed a level of playfulness this time that I had not detected in our previous chats. Maybe he figured out from my trip to the mall that I really would follow his instructions no matter what. Whether that was true or I was just wishing it were true didn't matter. I was soon kneeling on my chair with my ass facing the camera. I was leaning over the back of the chair trying not to spin around. My arms were reached behind me with my hands spreading my ass cheeks apart. Given that I had bought the anal kit, I assumed he was training me to be comfortable showing my secret hole.
He had me hold that position for several minutes. He told me his other sub was kneeling in front of him doing the same thing. He told me he was going to spank her while I paddled myself. I was jealous, of course, that he was playing with another woman. It was worse that he was doing it while he was playing with me. But subs don't get the luxury of worrying about those details. I just tried to stay still until he was ready for me to do something else. In a way I felt blessed that I was getting any of his time on a Wednesday instead of having to wait until Friday. After a few minutes of agonizing anticipation, he was ready to begin.
"I want you to lightly spank both your ass cheeks," he commanded me. "Start softly, move around covering your entire ass and gradually hit yourself harder."
I heard him begin to slap his real life slave. His voice distorter messed with the sound, I could tell from how hard he wanted me to spank myself and I did my best to mimic what I heard. His slave wasn't making any sound yet. I understood, as I wasn't experiencing any real pain. Sir explained that a light spanking served not to punish, but to increase the blood flow to my backside. He said warming up a sub first prevented bruising and allowed for a higher pain tolerance in the long run. I didn't know if that was true. I only knew my girl juice was running down the inside of my thigh because I was so aroused exposing myself to him. And to her, for that matter, if she was being allowed to see my broadcast.
After he told me her ass was pink, he instructed me to go to a mirror and check my own. I knew he could already tell from the webcam if I was prepared to move to the next phase of my punishment, but I guess he wanted me to see for myself. As I stood in front of the bathroom mirror I kept twirling around to view my ass from different angles. I must admit I though my slightly red bottom looked sexy framed by my black fishnet stockings. I hurried back to the computer and retook my position.
Sir had me spank myself harder now, but I don't think I matched his assault on his sub. That isn't to say I didn't try, but I don't think you can hit yourself that forcefully. I always slowed down just a bit before impact. After a few minutes I began to feel warmth spread through my butt and to my clit. I'd read that a spanking could have a very arousing effect and now I was starting to experience it. It was at this point that he ordered me to switch to the paddle. He also told me his sub was going to watch.
If it is a challenge to spank yourself hard enough with your hand, that issue goes away with the paddle. Maybe it is because it is an indirect contact. Maybe because I was so turned on and wanted to please James. Maybe it was the thought of another sub watching me punish myself as part of her training. No matter the reason, I was perfectly fine walloping myself. The first stroke stung like I'd never felt before. But it also made my pussy twitch. The second impact was much like the first. And I liked it.
Sir's sub reminded me to count out loud even though I had not her doing the same. I wasn't about to argue. I assumed he had a target number in mind, but I didn't ask what it might be. I was going to prove to myself and to them, that I was a good girl and could follow instructions. I was skeptical that warming my backside up slowly would prevent bruising. I was hitting myself too hard, I told myself. I wasn't sure how I would explain to John how my butt became injured. I guess would have to have to go back to blowjobs and missionary for a while.
The warmth from my butt had now spread throughout my body and my chest felt flush. I would have given most anything to play with my nipples right then. I had to fight to stay focused and not pleasure myself, even as James' sub taunted me for my lascivious display and obvious arousal. "Look at her cunt leaking," she exclaimed. "What a nasty slut."
Of course that just aroused me more. Sir was laughing at me as well commenting how easy it was to manipulate me into a compliant piece of fuck meat. At a count of 20 strokes I began to moan before I could vocalize the count. By 30 my whole body was quivering. By 40 I had enough and needed to cum. As I paused and turned my face toward the camera. I'm sure I had an expression of pure lust as I began to beg for permission to cum. I knew it would only take a couple strokes of my clit and a pinch of a nipple to get me off. I was confident my plea would fall on deaf ears. Perhaps Sir would stop my paddling, but I would have bet anything he would have another torture prepared to takes its place. Surprisingly that isn't what happened.
Well, maybe Sir had plans like that, but his sub interceded. I heard her tell him that I'd been good and that I should be allowed to climax. As a sub, I am sure she had been in my position before and knew exactly what I was feeling. Although I had never met her, I felt a kindred spirit, a sisterhood if you will, in her. I had been jealous that she was experiencing what I could not with James' hand on her ass and no doubt his cock in her holes. But in that moment, I only felt peace that she was looking out for my needs. Whether it was her intercession or his plan all along, Sir told me to sit back down in my chair, spread my legs and put my feet on the top of my desk.
That is how I found myself spread wide, dripping and broadcasting my most intimate needs to at least two people. James took control again giving me his usual instructions about how to play with myself for his visual benefit. He didn't let me come straight away, but he didn't make me wait too long either. Mostly he wanted to be sure I felt the pain and pleasure of sitting on a freshly and properly spanked butt. I have a padded chair, but it still hurt. But I didn't care. Thankfully he only made me tease myself for a couple minutes before he asked his sub for confirmation that it was OK to let me cum. She was agreeable so he told me to rub myself hard. I didn't need to be told that twice. I arched my back as the first waves of climax flowed like water through my body. It didn't matter that they were not broadcasting their own camera because my eyes were shut tightly. As my back relaxed I thrust my hips forward pressing my needy pussy toward the webcam.
"Oh God, I want to fuck you both," I yelled. I was lost in my fantasy world as my climax overtook me. I thrashed about in the chair and my legs fell off the desk. I almost slid down to the floor, but I managed to keep it together enough to avoid than inequity. When I finally did calm down I heard the unmistakable sounds of two people fucking. Distorted by his infernal box, but clear enough to know James was drilling his sub like a stallion. Now I was starting to get jealous because she was getting what I craved. I had to listen to them for about ten minutes. Well, I suppose I could have ended the chat, but I really wanted to hear her get pummeled. It also made me want to meet James as he was obviously as skilled in real life as he was online.
He made her beg in much the same what he makes me beg for my orgasm. To my ears she sounded a little better at it than I imagine I do. She does have an experience advantage over me. When he did finally grant her permission to orgasm, it was well worth the wait from my perspective. She clearly had a major league climax. I wondered if it was just from the fucking or if he had done other things to her as well. I could only imagine what else happened at their house that night. But I knew every detail about what I had done that day. It went into my journal and as I finally crawled into bed, exhausted but satisfied, my hand went between my legs thinking about her. Of course, if I accidently came, I would have to be paddled again. I smiled to myself.