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.