My Journey to Becoming a Mistress

On the second anniversary of the day we met. He asked me for a large sum of money since I manage his dollars now. He told me it was a secret and I would definitely be surprised.

I impatiently waited till that night. He arrived with a big bag. He sat next to me in bed and pulled out sluttiest dress that I had ever seen. He requested me to wear it.

It was so tight fitting and exposed ample cleavage. It barely came down to cover my panties and the bumps of my ass was so prominent. It made me wet when I saw myself in the mirror.

They money didn't make sense to me until he pulled out a jewelry box.

He handed me a thin long gold chain. He pleaded to me asking me to wear the key to his chastity device on the chain. I had almost forgot about it. It had almost been two whole months. I took it out of my purse. He helped me with the chain. The key now dangled between my breasts. He squirmed around telling me his cock may burst out of the cage when he saw this sight. I laughed out. I was genuinely happy.

From the look on his face, I figured he wasn't done. He told me he had one more gift and didn't know if I would like it.

He pulled out a small box. In it was a thin gold anklet. He explained to me that it would show his submissiveness and I should start wearing one even though I don't wear one now. He begged so hard that I decided I would. He insisted that I must wear it around my right ankle.

As curious I was, It did not take me long to get him spill the beans on what it meant. It did shock me at first. A normal woman would have drawn the line then and there. But I had grown used to his little surprises and confessions. I allowed him to continue. He went on to tell me it meant my partner was supportive of me seeing other men.

I was confused, filled with doubt. I even thought he was breaking up with me. It was a relief when he said he didn't actually want me to see other men. Rather it gave him the excitement to think that I had the power to do so.

It took me a day or two for that to sink in. I was still filled with doubts and still confused with his explanations. I doubted he was lying. Surprisingly he saw right through me.

That day before bed, he showed me a forum were New Yorkers with our similar interests hung out. He convinced me with a lot of threads that dealt with the situation I was facing right now. It was only after I had read different experiences did I feel more reassured that he really loved me.

The next day I proudly wore my anklet under my stockings to work. It was not flashy underneath the fabric. The chain around my neck was long enough to hide the key within my bra. I was surprised with how many noticed the change. The number of heads I turned that day made me feel quite powerful.

I decided to let him out of chastity that night. Ive never seen him that happy. He sighed in relief as I slowly stroked him.

Within a minute he ejaculated. The way he clutched my breasts , I knew it was a quite powerful orgasm for him. It took him a minute to recover. He kissed me deeply. He then gently kissed all the way from my neck to the tip of my toe before returning back to my pussy. I was extremely turned on. He made orgasm five freaking times in a row.

We lay back and I caught back my breath. He held my hand and begged me not to let him out of chastity for double the period next time. He claimed it increased his pleasure several fold.

We showered together and he locked it back on.

Our trust and intimacy deepened. Things changed from being a sexy role play to a genuine lifestyle.

He suggested we meet up directly with a few people into such a lifestyle. We had befriended this British couple Christa and Eric online. We met up with them in a BDSM club downtown. It was a strange place. One could see staged gang rapes, whipping and what not.

Christa was a very friendly person. We four talked over drinks. They had been following this for 7 years. They shared their experiences from way back when they were still dating. Now they were married, Eric stays at home full time. Christa works as manager in firm. She goes out with her friends, party late and sees other men. Eric fully supports this. He has allegedly has not been released in 3 years.

We did have a lot of questions for them. We found out that release from chastity was not the only way for a man to orgasm. Prostate simulation was a highly effective way. Eric explained how he masturbates by riding a lubed up dildo. He has embraced his femininity. I was amazed with all this information. He was literally the woman in their relationship.

Christa on the other hand gives Eric the freedom to masturbate whenever he wants. But she brings home other men she meets at a bar or dates for a while. She makes Eric watch or film her getting her brains fucked out if the guys were okay with it. She told us how she loves black men due to their massive cocks and unparalleled stamina. She dates exclusively black men and got herself a queen of spades tattoo on her ankle to openly advertise this.

Our meeting with Christa and Eric did change us a lot. We felt more confident with our relationship now rather than feel like an unorthodox couple. Thousands shared our interests.

We decided to take a page out of Eric and Christy's lives.

I began slightly flirting with other men just to become comfortable with it. He decided to stay at home and take care of the house. That meant he was naked all the time save his chastity device and his collar. I knew he loved me so it was quite easy to flirt without feeling guilty.

I helped him get comfortable with his prostate milking. He said it was painful the first time but I insisted he try consistently.

Within a month he told me he had the most powerful toe curling orgasm ever with his prostate milking. He told me it was a hundred times better than when he stroked his cock.

Soon I had myself a date. My first time I was going out on a date after such a long gap. I wore the same slutty dress he bought me. I let the key dangle outside between my breasts which were trying to burst out of my dress.

I wore a pair of sexy open toes heels and made sure my anklet showed. I had painted my nails bright red to match my red lipstick.

The power I felt as I stepped out into the street and I saw guys' jaws drop. Even the ones with their girlfriends or wives could not hide a quick glance.

My my. I have been going on and on for a long time. A lot more happened from that day to today. Five years from a pair of curious friends to being a married couple. More on that later.