My name is Cynthia and I’m a professional dominatrix by trade, but also dominant in my personal life as well. I met Robbie a few years ago when he first came to see me as a client. He didn’t have any specific fetish like most of my clients do. All he was looking for was to be told what to do it seemed. I tried a large variety of ideas to see what turned him on, but nothing ever worked. And he wasn’t suffering from erectile dysfunction either, because if I touched him in the way a girlfriend would he got hard.
After a while I did start to figure him out though. He mostly made one appointment every other week, unless the previous appointment was something that made him particularly uncomfortable. The first time this happened, I had tied him to the cross, placed his cock in a chastity device and then teased him with a feather. He started to get hard from the touching, which made the chastity device become a bit painful. He left that appointment seeming underwhelmed, but made another appointment three days later. A couple months later, we had a session where I dressed him up as a french maid and put him to work for two hours cleaning my dungeon with a vibrating plug in his ass. Again, he seemed underwhelmed, but made another appointment a few days later.
After that I started to get him and decided to try my hand at financial domination. During his next session, I put the chastity device on him, stuffed a plug in his ass and then put him in a diaper. Then I helped him get dressed and told him he was taking me shopping. If he refused to buy me anything I asked for, I would pull down his pants in the middle of the store and show everyone his diaper. I expected him to refuse, but he simply did as he was told. We went to the mall where I told him to buy me some quite expensive items: laptop, three pairs of shoes, two outfits, a watch and a few other odds and ends. He never once refused and carried all of my purchases to the car.
Back at the studio, I told him that he could return the items if he wished. I simply wanted to see how far I could push him. He said he bought them for me and I should keep them. We talked a bit more on a personal level, which we had never done before. Turned out he was a businessman that owned several local businesses: two coffee stands, a laundromat, a gas station and a small used car lot. He finally confessed that he was so used to being the boss that he simply wanted someone else to boss him around. Being bossed around was his fetish it seems.
Our sessions continued, but also became much more personal. We would often go out to eat or take trips to the beach or shopping. He began wearing the chastity device at all times. After a few months of that, he told me that he wanted me to take on the role in a more permanent manner. He wanted to marry me, but in such a way that it was quite clear I was in charge. He would sign a prenuptial agreement that stated that in the event of our divorce, I would retain ownership of everything he owned and he would be left with nothing. That way, if he ever refused my demands, I could simply threaten to divorce him and leave him broke and homeless. I agreed and we were married.
On our wedding night, I had a surprise for Robbie. I had purchased a special dildo with a row of bumps on the underside that were designed to stimulate the prostate. Keeping him in permanent chastity meant that he needed to be milked weekly to prevent a buildup that would cause him to become overstimulated and capable of orgasm. To consumate our marriage, I bent him over on the bed and buried the dildo deep in his ass. I fucked him hard until seminal fluid began to leak from his trapped cock. It was too much fun though and I continued to rock back and forth fucking him hard. When I was finally finished, I noticed that he had pissed a little as well.
I was quite upset that he had pissed on my satin sheets, so I paddled his ass and then grabbed an adult diaper from my stash of goodies to put on him. I made comments about being one day into my marriage and already had a baby. A new rule was created that night. He was to wear a diaper to bed every night to prevent accidents on my expensive sheets.
A few weeks later, after a thorough ass fucking and milking, I put Robbie into his night diaper and we went to bed. At some point in the night, he shit himself. Turns out I churned things up a bit with my dildo and he wasn’t able to control himself. Another new rule was added. Any time he wet his diaper, he would be confined to them for two days. Any time he messed in one, he would get a week in diapers. It started right then and he spent the next week in diapers. He was a bit concerned about visiting his businesses while diapered under his clothes, but he knew better than to refuse.
He was always particularly attentive when he was being diaper punished. Clearly he was trying to earn my favor and get released from punishment early, but it had the opposite effect. If diaper punishment made him attentive, then I would have to make sure he earned it more often. Whenever I was in the mood for an attentive Robbie, I would sneak a couple suppositories into his ass after a hard ass pounding. He rarely lasted more than a couple hours without shitting himself.
One time he had to nerve to let me know how desperately he needed to shit, hoping I would let him use the toilet. I pretended to be sensitive to his plight, so I laid him at the end of the bed and untaped his diaper. After pulling it open, he went to stand up, but I pressed him back down and asked where he was going. He gave me a confused look, then his heart sank when I pulled out a butt plug and lifted his legs to push it into his ass. As I taped the diaper back up, I told him that should take care of the problem. Of course it simply made it worse and an hour later he was begging me to remove the plug. He was given a choice. I could leave the plug and he could use the toilet in the morning or I could remove it and if he messed himself it would be a month in diapers. He chose to have it removed and promptly filled his diaper after I taped it back up.
Robbie now spends about half his time in diapers. I was tempted to make it a permanent thing, but then attentive Robbie would have no reason to come out. I quite enjoy the random massages and surprise gifts. He is currently taking cooking classes, so he can adequately take over the cooking chores. He already does all the cleaning and is often dressed in a skimpy maid outfit with his diaper peeking out under the skirt. He hasn’t had an orgasm in about two years and has spent very little time without the chastity device. It only comes off for doctor visits.
That is pretty much our life. I hope you enjoyed reading about it.