Brat Turns Boyfriend Into A Sissy

My boyfriend and I have been dating for probably three years now.  In truth, we couldn’t be any happier. We always had a lot in common, including the fact that spoiling me was high on both of our priority lists. I had always sort of gotten off on the idea of making him jump through all sorts of hoops, just to amuse me. In some ways, I could tell that he was getting pleasure from it, also. He even took on a second and then a third job just to try to impress me more and more. So it was going to be so much fun to turn my sweet boyfriend into a sissy. 

He always knew I had expensive taste. Yet he took each of my demands for more and more monetary investments in stride. In fact, he acted as if it was nothing out of the ordinary. While this was very rewarding in and of itself, it took the challenge of the whole affair away. Therefore, things became almost boring when I ordered him to bring me more and more expensive items for even a moment’s bit of attention.

Tired of Being Blasé

He could tell that his bratty babe was growing bored, so he tried harder and harder to impress me. Trying with the massive size of, what seemed like, his never-ending bank account. Even his exploding wallet full of hard-earned cash that was all for me wasn’t fun anymore. It was flattering, yes, but still, I really was quite bored. It became important to throw him off, shock him, really push his limits to see just how far he would go for me. I wanted to know just how kinky he would get for his bratty babe.

Choosing A Humiliating Fetish

I never really had to work since I was accustomed to everything being provided for me. My parents and any number of various boyfriends paid for my life’s needs and wants. One day, I was home while my current boyfriend was at work. Surfing some of the various fetish sites, I came across something that I knew was certain to push my boyfriend’s sexual humiliation limits for sure. I was so excited.  Immediately, I jumped up, dressed and headed out to the store. I needed to pick out some things for this very special night. Of course it was all on his credit card. Why not?

I spent several hours perusing the racks at my favorite lingerie and shoe shops. All the time, I was texting my boyfriend and telling him that I had something super-special planned for him. He kept trying to get more information about what it could be, but I was not budging. I loved being the  typical bratty babe. He was going insane wanting to know. Laughing, I just kept saying it was an ultimate test of his love for me.

His mind had to have been going insane trying to figure it out. I could see him checking all of his bank accounts, stocks, and bonds. It was probably his afternoon pastime. Of course, none of these were going to help him with this supreme test. Our time together was coming closer. I couldn’t wait.

Testament of His Love?

When he finally walked in the door, I could tell he was nervous, but he smiled at me. I was fully dressed in a cute pleated gray skirt and button-up lilac blouse. My outfit was particularly feminine. I was so excited, but managed to maintain my poise.

I asked him if he was, in fact, ready for the final test of his love and loyalty. Reminding him that he had done well up to this point, I wanted more of a sign of his commitment. In response, he carried on about how he would do whatever it took to prove his loyalty to me. Listing sexual proclivities I stored in my mind for the future, he said he would be put in chastity, be put in a chastity cage, even be  my cuckold! More than I had considered for this challenge. There is always the future.

Turning My Boyfriend Into a Sissy Boy

At this point, I gently took his hand as I smiled mischievously at him over my shoulder. Guiding him into our very posh bedroom, I wanted to show him the surprise. I had spent all afternoon shopping, just to surprise him!

As he looked down at the bed, I saw the confusion in his eyes. He looked at me, then at the bed again. Laying there was a bright pink lingerie set with matching stockings. A pair of shoes lay right next to the goodies.

I Got Him!

That was when I told him it was time for him to become my perfect sissy boy. He needed to learn that he is not a man, but just another plaything for me. Playthings include dolls with which to play dress up. He paused for a moment and I thought he might tell me,” No.”  But he reached down and started to get dressed as his cheeks blushed crimson.

Once dressed, he was clearly shocked and humiliated to be a sissy, but he stood awkwardly before me anyway. I could do nothing but laugh at him standing there, like a fool. What if this bratty babe sent him out shopping, dressed Just. Like. That? How funny would that be?

I loved turning my boyfriend into a sissy. Are you going to do the same thing to your boyfriend?

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