Dear Diary: Dressing Up The Sissie Boi Who Lives Next Door

The Sissie boi who lives next door is in the closet about his little kink and I’ve taken it upon myself to help break him out of his shell. On all outward appearances Robert looks like an up standing citizen. He’s powerful, successful and most definitely an alpha male. Or at least that’s how he wants people to perceive him. Not for long though, not as long as I have anything to do with it. When you’re a sissie boi, it’s imperative that you fully embrace yourself. Robert was simply afraid and it was my job to break him of that fear.

I stumbled upon Roberts little sissie boi second life, by accident as it were. Robert’s wife, Darlene recently hired me to clean their house as a way for me to earn a little of my own money (of course she doesn’t know about my naughty side gig as a phone sex operator) and for her to avoid dreaded house work. They both work during the day, so I just help myself in and do my thing. Well, last week I was feeling particularly vested in my work and wanted to get the place REALLY tidy.

While in Robert’s study, I noticed a suit case on the top shelf of his closet and I assumed it was empty. I went to grab it down, so that I could take to the basement with all the other luggage. It was MUCH heavier than I though and because of the weight, it just fell hard on the floor. It busted open and that’s when I realized Robert has a secret. His little secret was so over the top that I knew it would permanently change everything he had ever known. That’s when I decided to exploit this new-found knowledge and use it to my advantage.

The suitcase was filled with all the fixins a sissie boi faggot could ever want. I couldn’t even believe my eyes and frankly I had never seen such things. Butt plugs, vibrators, panties, bonnets,dolly dresses, Mary Jane’s, wigs, make up and much more we inside of that suitcase. I pulled each item out, one by one and studied it. Of course I took the suitcase home and hid it. You see, I took it mostly because I wanted to freak Robert out and because I wanted to make him squirm.

The following morning, after Darlene left for work I watched out of my living room window as Robert made a B-line right for my house. Part of my was so fuckin nervous and another part of me couldn’t wait to bust his kinky bubble. The best part was the fact that he didn’t even know what was coming. So there I was standing in my living room next the front door and before could even knock on the door I swung it open. Shocked, he just stood there like a man with a dick in his mouth and said nothing. I think that was mostly due to the fact that right behind was his suitcase, strategically placed in his path of sight.

I looked at him right square in his eyes and demanded for him to strip! He looked as if he was about to argue, but something must have clearly changed his mind and he obeyed. Once naked, I opened up the suitcase and picked out the most sissie boi outfit I could find. Complete with panties, stockings and a cute little dress. Now that my sissie boi was all dressed up and totally under my control, it was time to make him my bitch. His training began in that moment and we are currently working towards his acceptance of being my personal sissie boi.

Wouldn’t you like to hear about how good I fucked him darlin? More importantly, wouldn’t you like to hear about how good I am going to fuck you. Don’t let my innocent face fool you darlin. Deep down I am a dirty bitch and I will take full advantage of you. I will blackmail you, I will exploit you and I will make you the best sissie boi you can be.

Hanna