During the years we have played all sorts of games for my amusement and for Anne's torment. The idea is always more or less the same. I come up with an idea, something that I want to do or try out and then Anne will be my subject. Here is a basic one to give an idea what I mean and one that I have enjoyed and that has been often repeated. There are also different ones, some more advanced than others but I leave those for another story as each one is a story of its own.
These kinds of basic games or tasks usually happened during the weekend but sometimes during the weekdays. Mainly focusing towards the end of the week and on Saturday because any failures would then result in a punishment on Saturday evening maintenance. At the start of our relationship there were plenty of reasons to punish Anne but as she learned and got better I had to make things harder for her to get to punish her. I must admit I enjoy punishing her quite a bit and it would be a shame if she ever only received her weekly maintenance spanking.
The first thing I did was to have Anne wear different kinds of toys while she did her chores. For example to wear a remote control vibrator, a buttplug or sometimes both. Unfortunately the vibrator didn't have as big an effect on its own as I had hoped. It was hard to get one to stay on properly when she moved around and it was possible for her to notch it around and find a spot that it did not properly stimulate her and there was really no way for me to control that part and I did try a lot of different kinds of vibrators. The buttplug on the other hand worked much better. We had been using buttplugs during sex but she had not had to wear one for extended periods of time or to really walk or do anything with one. At the start even a small plug made a huge difference. Anne had some trouble even walking around with the plug and it clearly felt uncomfortable when she tried to do any activities or chores. The buttplug combined with the vibrator also made the vibrator work much better as Anne had to compensate more for the plug and could not focus so much on the vibrator. Of course after some time Anne got used to the buttplug and how it felt inside of her ass but I could always increase the size to keep the desired effect and I did.
I gave Anne all sorts of tasks to do while having the vibrator and/or a buttplug inside of her. They ranged everything from cleaning duties to entertaining me with a striptease. I also often gave her a time limit because it wasn't that she could not do the desired tasks while plugged but rather they took more time and effort. At first the times were off quite a bit but soon I started to learn and was able to give the task and the time so that it was doable but only barely. I loved it when she missed her goal by just a tiny bit and she knew the task was totally doable but she had just failed. Just giving an impossible task is not fun and there is no game aspect in it. I like it more when Anne knows she failed and next time she will try harder. Of course I would mark up the failures and then administer the correct punishment during the maintenance.
I think it was the second time I had Anne wear a buttplug and a first with the vibrator when I had her clean our toy cabinet and all the toys and instruments. I asked her how long she thought it would take and she estimated it would take her 2-3 hours and that was before she knew she had to wear a buttplug and a vibrator. I told her to dress up in a maid outfit that had a tiny black and white dress, white stockings, a headpiece and black high heels. When she was ready I showed her the plug and the vibrator and told her that she also had to wear these. I had her bend over the desk and with the help of a little bit of lube I inserted the buttplug in her ass and the vibrator in her pussy and on her clit. She was allowed to wear panties to better hold the vibrator in place. I told Anne that she had 1½h time to clean everything up including washing up the toys and instruments and organizing the cabinet so that each item would be in its correct position. Of course Anne is required to clean up the toys after each use but the whips, ropes, restraints etc. don't get to be cleaned after each use but are cleaned every now and then.
Anne protested that there wasn't enough time to get everything done but I told her that she was wasting her precious time arguing with me. She sighed and then quickly got to work. I took a comfortable position in the armchair and watched her work. Anne had real trouble walking with the heels that went with the maid outfit while her ass was plugged. Also bending and reaching seemed to be tough. She had to run to the utility room to wash stuff and then back several times that really seemed tough for her. In the meantime I played with the vibrator controller to change the rhythm and try to catch her off guard with it. I must say it was a ton of fun.
All good things must end and finally she was done. I got up and proceeded to check her work. She explained that the ropes were still in the utility room drying up with some of the other instruments. I approved that but noted that some of the toys were in wrong positions and that one of the whips was missing. She had forgotten it in the utility room when she had cleaned it. Also it had taken her 1h 43min to be exact.
I told her that she had made four mistakes. One was the missing whip, second was the misplaced items, third was running over the given time by 13 min and the fourth was that she had estimated the time so much off to make it too easy for herself. She had predicted 2-3 hours before any handicap when she could have done it easily under half of that.
These mistakes would get her extra punishment for the weekly maintenance. 2 hits for the missing whip, 3 hits for the misplaced items and one for each minute over the time limit to the ass, total of 18 hits. The time estimate, that was so much off in her favor, was a larger mistake and she should come up with more accurate estimates in the future. To make a point it would result in 5 hits on the breasts. This was all on top of her maintenance and what else she had accumulated during the week, which was 8 hits on the ass.
So in the evening Anne was to receive a total of 36 hits on the ass and 5 on the breasts. I decided to change 10 hits from the ass to 5 on to the breasts so the total score was 26 on the ass and 10 on the breasts. I really like to whip her breasts. This was quite a bit more what Anne had been used to as there had been several occasions when she had just received her maintenance punishment and lately the extra punishments had been below 10. Anne was clearly nervous about the amount she was to receive, especially about the 10 hits on the breasts.
The time of her maintenance came and she entered the bedroom as every Saturday. She told me her mistakes and I told her the punishment. She then took off her clothes and took position over the whipping bench. I took a riding crop from the cabinet and proceeded to start with her ass. Anne took the first 10 hits very well, even though I hit quite hard, as she has got used to the weekly maintenance. The next 5 she also took well but after that the hits started to take their toll. At number 17 she started screaming and at number 19 she had trouble keeping still. I warned her not to move and somehow she managed to receive the rest. After 21 she teared up and the two last ones made her cry. I gave her a moment to calm down and then told her to kneel on the floor. I told Anne to hold her breasts and support them from below. I pulled her head back so I had room to operate and my first swing hit right across the breasts. Anne managed to take two first hits well but already the third made her cry out. After five across the breasts she started to tear up. I changed my aim to her nipples and the sixth hit her right nipple. Anne screamed out loud and I took aim again. The seventh missed the left nipple just a bit but hit the areola but despite that Anne screamed just like before. I took better aim and the eight found its mark on the left nipple that resulted in yet another scream. At this point Anne started crying. I took aim again and managed to hit both nipples at the same time with the ninth and tenth hit. Both were rewarded with a loud scream from Anne. After the punishment was done Anne thanked me for it and I had her suck me off while I took my position in the armchair.