Sequel to My Online Kink Match Part 1

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This is the sequel to my previously posted story My Online Kink Match and takes up where that story left off.

Dear Jay D,

I thought that after my long letter to you I would update you one where things stand with the three of us. As you might remember, Barb had just joined the two of us in the scene we have. He had just given me an expensive girt of piercing my nipples and labia with rings, a lovely large set of golden chains, bells for my piercing as well as a tag identifying me as a slave to him. At the same time I became the Mistress (under instruction) for Barb who was submissive to both of us.

I woke the following morning from a deep slumber feeling very refreshed and earlier than the alarm was due to go off. School for the kids had started and normalized our schedule a little bit. During their summer vacation, things are always more hectic with all kinds of car pooling and different sports. Now they were in school, things naturally settled down. Additionally they primarily play summer sports like baseball and school sports in the fall, winter and spring. That keeps them on one place for most activities. I knew that I had some issues that needed to be addressed today. On the way home last night, before we left the hotel, he had given me several things to make sure I was prepared for my new responsibilities as Barb's Mistress. First he gave me a Limited Credit Card which he wold pay the bills for. I was limited initially up to a thousand dollars and he would monitor it online and pay the bills as they came in so as long as the bills were for my Mistress duties, they could be paid. He also gave me a duplicate of his Blue Duffle although mine was red. Inside it was a set of canes, paddles and other implements including the devices for Barb's training. Also included were heavy rubber bands, and basic things like lube, soothing gels and lotions, condoms, ropes, cuffs, straps, a posture collar, blindfolds among other stuff. I was well prepared and I had stashed that all in the car trunk after the kids went to bed. He also gave me a set of instructions of how he wold like me to proceed in the near future. I should game out various fantasies for Barb to live through and they were to be of my own choosing. I was to look at costumes I could find online from sites such as Amazon and adult website. I was also to at least do basic research on PonyGirls and the groups they were associated with and what equipment that might be needed for that fantasy. I was to write out , over the next few weeks a business plan for putting together a podcast for the two of us to host including equipment and help that we might need and also what we needed if we wanted to open a channel or OnlyFans area for Barb to use. Obviously he had listened when I had talked about those ideas to him last night. Finally he wanted me to brainstorm out with Barb other things so that she had some input as well just as he talked with me. We would plan on Tuesdays as reserved for the two of us in the future unless scheduling conflict came up, Wednesday nights for me and Barbara and him until he felt I could go alone with it and Saturday nights for Punishment nights. All of these were subject to schedules obviously. Those were the issues he provided for me to take care of. AdditionallyI had to make the reservations and arrangements for Wednesday nights with Barb and keep him informed. If that was not enough to keep me busy, I had issues that had to be dealt concerning Barb. She had already broken the rules by answering requests and chats online and I knew other things were going to crop up as well. Even so, I felt very confident that I could handle all of that.

Right now I was more interested I remembering last night and how good it felt to me. I would game out my lunch with Barb later to deal with her issues, make the arrangements for the low impact session for Barb tonight knowing she was all set already with her SchoolGirl uniform. So I lazed in bed for a moment remembering with my hands between my legs. It was quiet in the ouse except for m heavy breathing.

I was up well in time to get breakfast on the table and was thinking the entire time how to handle Barb at lunch. I booked the same hotel we normally used online and got a discount as well. Then I started thinking about the session as a whole trying to make sure we used the time wisely. At the end of the session I intended Barb to be a well chastened lady. She must be punished not only for her failure to learn her lessons which I knew wold be the case but also for her breach of discipline. She would be sorry she crossed me. We wold all meet at the hotel, me fif*** minutes early, a t 6 pm. I knew he wold be early was well. I made sure the kids had dinner arranged and all pickups to be done b the oldest who was a driver now and had football practice to go to. The other two would hang with a friend until he picked them up after practice. This was not an unusual event for any of them.

I texted Barb to meet me for lunch. Then it was a rush out the door for all of us, the younger ones catching the bus, the older one to pick up friends and me to go to work. I checked that the blue bag was safely in the trunk.

I was surprised at work when I received a promotion. The other workers surprised me a cake. The promotion was a blessing since it would ease my financial situation and the work load seemed to be easier than what I was doing although not nearly as mindless. I was flying high today.

I made sure that we were in a booth at the back for lunch since I n=intended to scold Barb. When she came in she was sheepish and I realized that she must have started to understand what she had done wrong. She tried to apologize but I just simply told her I was going to get my pound of flesh that evening. I reminded her that she had better be studied up on the test and answers I had provided to her and I told her to be precisely on time. In my mind I predicted she would be late but time would tell. She was to wear her new outfit and it must be precisely fitted to her. She agreed she would and appeared to at least be a little remorseful I lectured her that it was for her own good. She did not want to get scammed or chatted by all those bots and fake accounts They wanted her Personal Information and would use it to scam her. At least she pretended to agree and would not do it again. At the same time she wanted me to look at the people she had responded to since they were do hot. She did not understand that fake accounts came with fake pictures and the masterminds might even be just some high school kids punking her at best but also could be real professionals in the scam world. She just did not believe it, She thought everything was real online. I assigned her to research online scamming on dating sites by using her search engine at work so she could see this was
serious stuff. No moderator could possibly keep her safe if she was doing stupid things. I again warned her to stay away from any profile that was not fully filled out, had only a single or just two or three pictures, and any pictures that were just too good to be true. I didn't care about the dick pics or the lewd comments. We could just ignore those. She would get into trouble by herself if she answered or reached out to just anyone who looked good. She needed guidance. Reluctantly she again agreed to all of my rants at her. We did not dish about my session the night before since I intended to surprise her with my new piercings and chains. Instead I deflected her questions by asking her what fantasies she wanted to live out. She shocked even me with her salacious suggestions most of which included large dicks, groups of people, couples, and copious amounts of semen. Like I said, she is both a slut and and attention whore. As we left I reminded her not to be late.

I arrived a little earlier than I planned so I had already had completed the set up for tonight by the time he arrived. Her spot was outlined on the floor, the cooler was out with water, for her, beer for him and wine for me. I was dressed to kill in my mistress dress and had the chains hooked to my rings on my body. Chairs were positioned correctly. He would sit in the corner just to watch but could take his satisfaction before I did at the end of the session. He also said he would help with the camera. He sat down in the corner chair and I got him and a beer and myself a wine. He pulled me to sit in his lap as we chatted about tonight and other things. He took advantage of my chains and pulled my breasts out by the nipples out of my low cut dress. He fondled the and played with my nipple rings as we chatted. Neither of were very perturbed by the realization that Barb was late. When the timid knock sounded, I went to the door and opened it with a scowl on my face to see Barb looking scared again. I gave that no regard but hissed at her “Your late, cunt. I will not countenance it. Get in here and get prepared for the beatings of your life.” She grimaced as I did that and came in fast. I closed the door and stepped out of my dress exposing my breast like a pair of torpedos on a platform and my bare pussy framed by the two forward rings in my labia. My nipples were fully erect and the large rings stood out. She did not see them since as she was staring straight ahead. I walked by her and settled into my chair for a moment until she got to her spot, turned to face the bed, put her hands behind her head and stood on her tip toes. I liked the ways her legs strained as she did so and I knew it would be difficult to maintain that posture as we got started. I got the cuffs on her and made sure a gag was available since I figured she would make noise. I inspected her uniform and of course the tie was not on correctly and when I checked under her skirt she was wearing thong. It seemed she was really cruising for a bruising and boy was she going to get one. This tie I did not bother to give her any warm ups. Instead I had her take the punishment position and pulled the thongs down after I piled her skirt on her back. I figured we would just go ahead and start with 25 strokes for being late, the stuff online and the uniform infractions. By the time the fifth stoke landed she was wailing so I gagged her. I beat her as hard as I could. I wanted to make sure she was well beaten before we got to the test. She was already crying and tear streaked when I finished and her arms were shaking already and we had just started. After the caning I worked her ass over with a strap to ensure she would be nicely welted with wide welts and then proceeded to paddle her raw to provide those nice deep purple bruises. Finally I felt we could start the session. Had her stand in the attention position on toes and made sure the tape was attached to the heels of her feet. I was not going to miss a chance to punish her and I knew she could not stand there too long. I decided to let the first lesson sink in while we took pictures of her standing like that and then he and I had another drink while we watched her wobble. Sure enough she put her feet down and earned another five strokes of the cane and a stern lecture. Then I took out the switch bundle and the switches.

She had not yet experienced the switch bundle which gives off a very different kind of coloring to your bottom. The fist stroke never seems to be much but in the end, her bottom was mottled with little marks where the stem ends of the trimmed stems jutted out of the switches. It would add some interesting color for the next few days and her loins were well marked as well as her thighs. At this point, I thought she was ready for her test. Certainly she was now sobbing hard enough for her shoulders to be shaking.

I checked in between her legs and sure enough there was a lot of cum starting to flow and she did not have the devices in her as yet. You could see cv she was very wet and I rubbed a switch roughly along her slit and it away wet. I twirled a little string of cum that was hangin down from her on the switch. I knew the little nubs of stems probably excited her more as she waved her ass at me as I did it. She truly was a super slut. I switched inside her thighs just for good measure and to give her some things to remember in the future. When I watched her I decided she really needed to cum and had mercy on her. I removed the gag and reminded her that she was not to cum without permission. I made sure he had gotten the cum inside of her thighs on camera and then he handed me the devices. I rammed the butt plug unceremoniously into her. She groaned loudly but did not complain. Then I put the combination device into and on her making sure it was secure with a strap. He had control of the remotes and I whispered to her that I was going to cane her to completion and again warned her not to cum without permission. She groaned when I told her that and I picked out the most severe cane of the bunch. It was heavy and would cut into her ass and thighs deeply. The first strokes came up beautifully with deep purple cuts aligned with red lines running alongside. She was seating through her little girl blouse as I beat her and her hair was wild all over the place despite the ponytail it was in. I could see she was in very deep *** but although she was moaning and groaning, she did not say anything or yell. I left the gag out of her mouth. After about ten strokes she was asking to um and I denied it and he just fiddled her down a little so she would have to take more punishment. By the twentieth stroke she was faltering and I could see her arms were not going to support her much longer. He moved a pillow under her to help catch her when she fell onto the bed which must be soon. It was and her arms gave out and she writhed on the bed as I caned her ass over the pillow that supported it. I could see the wetness flowing around the dildo and I nodded at him and he turned all units up to full and random. Now she was really writhing. I denied her once again and she gushed all over the floor, pillow and bed. I had never seen such an orgasm. She went limp but was still shaking hard when we rolled her onto the bed fully, I used my rubber bands while the devices were still in to get inside her most secret places, snapping them hard. I wanted a little revenge. When I was done, we each got a drink and sat by her as her eyes rolled in her head and she started to calm down I rubbed a cold water bottle on her forehead to cool her down. As she recovered I made her drink some sips of water and held her head in my lap. Finally she had calmed down enough we thought she could continue. We took off her blouse, skirt and little girl bra. The thongs was long gone, discarded into a waste basket. We sat her on the side of the bed and I decided I would not do anything to her breast since she was still badly marked. I did bind them however with rubber bands and decided I would use a switch on them before we stood her up. Right now she was still too wobbly.

I finally decided she could stand and we got her back up standing. I retrieved the test questions and answers for her and decided I would give the entire 200 but would use a switch instead of a cane to teach her the answers. It was clear she had done little to prepare so my notion to use the switch was good since she missed almost 60 percent of them getting to two strokes per question. She was well switched when it was over and again sobbing and again getting excited. I sat her down on the side of the bed and switched the top of her tits long and hard and then had her lie down so I could get underneath them. I pulled her breasts upward by her nipples causing her to squirm as I did so and then switched each one in turn underneath making sure to get in the crevice between her breasts and the rest of her body. By the time I was done, her breasts were criss crossed with the switch marks. I knew they would last a long time since they burst the capillaries.

It was now time for her to give us some satisfaction. I bowed to his needs first and of course he had decided he was going to take her in the ass. It was rerun of the other night except he wanted me to get more closeups of her face as he did her. The butt plug was pulled out after I got him hard with my mouth and put the condom on him. He put some lube on his cock this time and it went in easier and with less of her complaints although she groaned loudly the entire time. He mad her admit he was in her ass and that it hurt. All of that as her face was framed by the camera video . Since I watching her face I noted her anguish and how difficult it must have been for her as her face contorted from the *** in her stomach. When he finally finished she was sobbing and tears were rolling. She was a mess and I allowed her to rest while he went to the bathroom to get rid of the condom and clean himself up. When he came back in I took my seat at the edge of her spot and motioned her to kneel in front of me. I was a very demanding Mistress as she lapped into me, finally noticing my rings for the first times and her eyes grew round as she looked them over. I made her do me deep as well as making sure she got me all around my sex and all the secret spots. I found her ponytail to be a great aid in guiding her movements. It was almost like having a handle on my own vibrator as I guided her tongue around. When she was not performing well I switched her a little on her back or tits. I managed to get some switch marks on the side of her tits that we pretty deep. Finally I came as well as she lapped it all up. When I let go of her ponytail, she sat backwards on her legs and looked she was truly exhausted. She could hardly move. We moved her a moment or two later and actually had to lay her down over the side of the bed. We reinserted the butt plug and I caned while she was lying over a pillow. When she finally came again she again spattered the bed, pillow and floor. This time she was out for a pretty extended amount of time. We sat with her as she shook and her eyes rolled back in ecstasy. We each had another drink while we waited. I held her as she started to wake up and he started to clean up the room which because her cum was a mess. He packed things up and we were ready to go before she was. He carefully made sure the pillow covers were off and in a pile as well as the towels he sued to clean up the rest of the mess. We allowed her to clean up but she was still a mess as she dressed back up in her SchoolGirl outfit and stumbled out the door again refusing our assistance to her car. We might have been negligent in allowing her to drive in that state but I figured she would recover fast when she got back to the car. I wondered how my favorite clerk viewed her when she went through the lobby. We sat and drank the rest of the wine and beer before we left and discussed Barb's future. I had done my research into PonyGirls and was impress by the dedication they had and it actually looked like fun if only for the elaborate outfits they wore. I thought it would be a great fit for Barb. Besides, I wanted to drive one of those neat little carts they had. I could just see her running around a track or dirt road while I was behind switching her in my little cart. It might just give her a larger sense of humility as well. He already had our names in for the Halloween party at The Honey Be Bar and I was going to have decide how we did a combo act on stage. At the party things were even looser that special occasions I was informed and I could actually play the part of a mistress as long as I didn't make it too rough but I could spank her and cane her or do almost anything I wanted. I cold even have sex with her if I wanted to. The doors would be locked. All of this was in front of an audience of course so it meant I had to think about it. We would both be expected to waitress with the usual benefits and groping. I wondered if Barb would sneak in some time in the private rooms even if I forbid it. The event went to the wee hours of the morning and of course the entire rough crowd wold be there with wives and girlfriends. I knew I would have to warn her not to get into with any wives or girlfriends though I doubted it would do any good. I suggested perhaps we should just short circuit that by having some fights between the girls with Barb that were controlled. He lifted his eyebrow at that thought. God help me but aI also suggested we could get a small kiddy pool filled with oil and even stage whip fights like the PonyGirls do. That really raised his eyebrows. He in turn thought we should even have rules and make it formal that a girl could challenge another girl to the fight they wanted and if the challenge was not accepted the girl challenged had to leave the premises. I wonder if I had just made things worse.

When we finished our drinks ( I was not punished since I was really a night off for me) we walked to my car and piled the stuff into the trunk He reminded me to make my formal request for Saturday night and be careful on the road. We kissed and cuddled for a moment and he tugged my breasts out by the chains again as we did. After some fondling I got them back in the dress just as a car pulled into the parking lot. We kissed again and drove home.
The kids were all up again as I got home and hooted and whistled at me when I walked in wearing my dress. I blew them all kisses and smiled. I got them ice cream for being good and when I went to my room I took out my stash of cash and thought about how to spend some of it on them. I decided that we wold go to one of those splash adventure places while it was still warm. They loved swimming and it would tire them out on a Saturday before our punishment session. That would mean they would likely be in bed by the time I got home. They deserved a nice reward and I would spend less than a fourth of the ***. Times were still pretty tight in our household but I could do that and still have some emergency funds.