In the past I had inserted a tampon and wore it for between 30 minutes and 2 hours. I had mentioned this to my girlfriend / Mistress in the early days of O/our relationship.Back in May of this year She rang me at work one Wednesday evening and told me that I needed to go and do a bit of shopping as She was setting me a task. She told me that I would be required to wear a tampon on Saturday from 9am till W/we were ready to go to bed that night and as such the task She was setting was a tampon training task to get me used to wearing a tampon for long periods of time. This immediately got me very excited. She told me to go and buy 2 boxes of tampons, 1 regular and 1 super, a tube of lube, a packet of panty liners and a pair of size 12 / 14 purple nylon / elastane women’s panties along with some new blades for the razor that is used to shave my **** and balls and that I was to ring Her when I had the required items. I really enjoy being given tasks of a sexual nature and thanked Her and set off for the local supermarket to purchase the required items. By the time I had got the required items and returned it was just after 7:30pm. I rang Her as instructed. Knowing that I work till the early hours of the morning and that I work for myself She told me to go out to the back room and to take my purchases with me. She then instructed me to remove my jeans and briefs and to put a little bit of lube on my middle finger and finger my ******* till She told me to stop. Then I was to shave my ****, balls and ******* before inserting a regular tampon so that it was positioned just past the entrance to my *** and put a panty liner in the purple panties and put them on. Then I was to put my jeans back on and get back to work. By this time it was 8:00pm. She told me that the tampon was to stay in for at least 4 hours before I could remove it at which time I had to take 3 photos of the tampon from different angles and email them to Her and I was not allowed to *** or I would be severely punished. I thanked Her for Her instructions and hung up. Just after 12:30am the tampon was beginning to cause me some discomfort so I removed it and took the required photos and emailed them to Her as instructed. It felt good to have the tampon out. I was extremely hard but I dared not ***, as I wasn’t sure what my punishment would entail. When I sent the email I noticed that She had sent me an email just after I had hung up earlier, and the subject line said: Don’t open until you have sent Me the photos. Since the photos were sent I opened the email. It contained further instructions to be followed up until Friday evening when W/we would be together again. In it I was instructed to take the purple panties, a panty liner, a regular tampon and the lube home with me as once I had showered in the morning I was to repeat the procedure from last night with the exception of shaving, and I was only to use the lube if it was absolutely required. This time I was to wear the tampon for 6 hours at which time it was to be removed, I was to hold it under my nose and smell it for 1 minute, then take the required photos and email them to Her, and after an hours respite I was to insert a super tampon for the next 6 hours. If I needed to go to the toilet I was to do it in that hour break. The tampon went in with out any lube and was in at 9:00am which meant a 3:00pm extraction, by then I could really feel it. When I pulled it out it was fully expanded and coated in poo. The smell wasn’t as bad as I thought it would be which made this part of the task bearable. I took the required photos and emailed them off before taking this opportunity to go to the toilet. At 4:00pm the super tampon went in, with a smear of lube on the entrance to my *******. At 8:00pm She rang me and asked me how I was going. I told Her that I was coping but I was extremely horny. She asked me if I wanted to jerk off, I told Her that that would be greatly appreciated but I didn’t want to be punished. She made a deal with me. If I wanted to jerk off it was OK, but I would have to nominate a punishment. I thought about it for a minute or two, then agreed that it was a fair deal. I told Her that She could give me 5 strokes of the cane on my bare *** before She removed the tampon on Friday evening. She agreed and added, that when I removed the tampon tonight I would be required to smell it for 2 minutes before taking the required photos, to which I agreed after thinking back to this afternoons tampon. Then She said something that caught me by surprise. She told me that the photos looked good, and that if I wanted to jerk off tomorrow when I changed the tampon the new deal would be after the 5 strokes tomorrow evening, since I was getting used to the smell, it was now time to taste the tampon. Once it was removed I would be required to put it in my mouth and suck on it regardless of how dirty it was while She gave me a further 10 strokes of the cane. I don’t know what came over me but I agreed without hesitation. With that She said goodnight and hung up. At 10:00pm I removed the tampon, smelled it for the agreed 2 minutes, took the photos and emailed them off. Then thought about what I had agreed to and began hoping that Friday evenings tampon came out clean. I had a restless nights sleep and couldn’t stop thinking about what was going to happen. I was up at 6:00am, the tampon was in by 7:00am, which meant a 1:00pm change, but today the new tampon was to go in straight away with no lube and a 3 minute smell before the photos were taken and I could jerk off. What an amazing ****** I had. I left work at 5:30pm; the movement of my body as I was driving kept the tampon foremost in my thoughts and kept me extremely hard. The afternoon traffic seemed unusually heavy, or was it just my level of arousal playing tricks on me. I arrived at Mistress B’s place just before 7:00pm. She had the punishment bench set up and waiting for me. She welcomed me and ordered me to ***** and position myself over the end of the bench, and hand Her the cane that was on the bench where I was to lie, as my punishment was imminent. She teased me for being hard and gave a tug on the string hanging from my ***. She asked me if I was ready and brought the cane down on my poor *** with a crack, OUCH that hurt, I nearly expelled the tampon. There was another crack as the cane bit into my *** again, 3 more She said, WHACK! And again CRACK! Only 1 more before you get to taste your tampon She reminded me, like I needed reminding. Whoosh CRACK, done. She blindfolded me and told me to push as She removed the tampon. Then gave me a few minutes to regain my composure before She told me to open my mouth to accept the tampon. I had no idea how dirty it was due to the blindfold. The smell was familiar, I thought I might be sick but I was OK, it tasted strange but by the time She had finished giving me my 10 strokes I had gotten used to it. I wouldn’t say I enjoyed it but it was bearable. She thanked me for taking my punishment without fuss, and told me that my tampon training was complete. She told me that She noticed a bit of blood on the tampon and as a safety precaution Saturday’s session would not occur.