Little Sissy Bitch

little sissy bitch

Bob was one of those bosses that everyone avoided whenever possible.  Everyone knew that it was best to stay off his radar and definitely out of his office.  And God help you if you ended up in there alone. We women, and really most of the guys too, tried to look out for each other and warn newcomers to our office about him.

Not only was he a bully, but he also used whatever means he had at his disposal to blackmail and threaten women into providing sexual favors.  Every time I saw a woman leave his office straightening her skirt and fighting back tears, I fantasized about stopping him for good. But I never dreamed that one day I would make him my little sissy bitch. 

A reign of terror – office style

Lately, Bob left me alone, for the most part.  He knew that he was incompetent and lacked any management skills or business knowledge whatsoever.  And for better or worse, I picked up his slack and kept the office running successfully. This, of course, only allowed him to continue his office reign of terror.  Oh, and did I mention that he was the Company President’s idiot younger brother? That meant that complaining about him would hurt you much more than it hurt him. The situation seemed hopeless and I desperately wanted to change that.  

And then one day I had enough.  Emma was the new girl in the office.  She was sweet and kind and still in college. Although she was smart and ambitious, she was also a bit naive and innocent.  But most notably, she was absolutely gorgeous.  Blonde, big blue eyes, big beautiful tits, and a round perky ass.

At least he doesn’t last very long…

Bob, of course, took a special interest in her.  Despite managing to avoid it for quite a while, Emma ended up in Bob’s office alone with him one afternoon.  Just a few minutes later, I saw her shamefully leave his office in tears with Bob’s cum all over her face and in her hair.   She was holding her blouse closed and pulling her skirt down as she hurried back to her desk. “Well”, I thought, “whatever awful things he does, at least they don’t last long…”

Almost everyone had left for the day so I went to her desk to check on her.  She said that as soon as he reached around her and locked the door to his office she knew she was in trouble.  He ordered her to strip naked and bend over the desk so that he could fuck her. She begged him not to – saying that she was a virgin and was saving herself for her fiance on their wedding night.

At least the little sissy bitch has an unimpressive dick…  

So he grabbed her by the hair and forced her to her knees.  He unzipped his pants and said that she needed to suck his cock instead. He held her head still and shoved his below average sized dick into her mouth where it mercifully didn’t even come close to reaching her throat.  About one minute later, he pulled out of her mouth and came all over her face. 

It was then that I started to plan. I wanted to make him suffer, submit and feel the same humiliation and shame that we all did. But realistically, I mostly just wanted to get him fired and to give him a taste of his own medicine. But it of course turned into much more than that.  This is that kind of story – a little sissy bitch story. At some point, I changed my mind and I decided that I wanted to break him. I wanted to keep him captive and somehow make my boss into my little sissy bitch.  

Up next:  Well, what do you think of the story so far?  

I know it’s a little different than the last one – the satisfied slutty captive.  It’s almost the opposite, in fact.  Except with more kidnapping and less consent.  Most importantly, how do you even start making your boss your little sissy bitch?   Stick around and we’ll figure it out…

little sissy bitch

Want to read more of my sex stories?  You can find me here…

And if you want to talk about being a sissy boy, need a bit of my own special brand of sex therapy or anything else just call me for the best phone sex you will ever have…