Ok well, Monday morning got there fast and I was getting ready for work, but scared to death that Mr. Smith would out me. The phone rang.
“Good morning Maggie, it’s Mr. Smith.”
Oh my god, I thought.
“Yes, Sir,” I said.
“I want you to wear a pair of thigh highs and panties under your pants, do you understand?”
“Yes, Mr. Smith,” is all I could say.
I had to get going soon so I ran upstairs and pulled out a pair of purple lace boy shorts and a pair of purple thigh highs. I put my purple garter belt on then the stockings and pulled my panties on. Finished getting dressed, I drove to work.
Sitting at my desk like that I thought everyone could tell I was wearing my girly things. I was so scared I wasn’t paying attention. But then Mr. Smith walked in and from what I could tell he didn’t even look at me. About an hour and a half later I got a call from him.
“Maggie, come to my office please and shut the door behind you.”
“Yes Sir,” is all I could say.
I walked in and shut the heavy door and locked it at his request. I did as I was told.
“Now lose your pants; I want to see if you can follow directions.”
I did as told, revealing my purple garter and panties and stockings. Then the next thing I know his flash goes off, he took a picture of me.
“What the fuck?” I said.
“Blackmail,” he said with a smile, “your my slut now, do you understand? You will do and wear what I tell you. When I tell you to come over dressed you will be on time wearing what I tell you. Is that understood, Maggie? Because if you don’t, I will show everyone in this office what a sissy slut boi you are!”
“Yes Mr. Smith, I understand”
I keep wondering how I got myself into this.
“Good. Now get over here and get on your knees and suck my cock! I have not cum since Saturday morning in your ass!”
Doing what I was told, I dropped to my knees in front of him. His cock was already out and semi hard. I slowly sucked his cock as I played with his balls, he took forever to cum. But when he did it was all I could do to swallow it all.
“Very good sissy! Now get dressed and get back to work. Oh and you will be stopping by my place at nine tonight! Wear something slutty!”
After work I ran to the mall; I only had the one dress, I needed something else. I went to this store that sells mini dresses and stuff, I found several dresses on sale and bought three of them. I then raced home to get ready, arriving at nine I knocked on the door. Mr. Smith opened the door wearing just his pants, no shirt. God I loved his chest, so sexy.
“Come in, slut,” he said.
I walked in and was ordered to go to the living room.
“Bend over that table,” he said. “Elbows and palms down and ass up.”
I did as told as, he was getting things from a drawer. I couldn’t see what he was doing. Then he walked up behind me and told me to stand up. I did as told and he placed a ball gag in my mouth and then cuffed my wrists behind my back.
“Bend back over, slut.”
I did and he pulled my little mini dress up, then my panties down just below my ass. I then felt something cold against my boi pussy. He shoved a large butt plug into my ass, then pulled my panties back up.
“Keep that in, Maggie!”
He then got out a leather paddle as he slid it across my ass. Then SMACK! I felt the sting!
“Stay still, sissy, I am not done.”
I got ten smacks across my ass. He then walked away telling me not to move. When he came back he had his black leather mask on. He ordered me to stand up. I did and he took the cuffs off, turning me to face him he cuffed them in front of me. He then told me to walk towards the window. I got half way there and he said to stop. There was this chain thing hanging from the ceiling. He lifted my wrists up and as he stretched them I was almost on my tippy toes. He hooked the chain to my cuffs, and I almost dangled there.
He then set up a video camera and in a disguised voice said, “This is sissy Maggie, he wants to be fucked like the little slut that he is.”
He then stood behind me and pulled the butt plug out, my panties down around my ankles, my dress lifted up around my waist, my little hard clit growing.
To the camera, “This is what Maggie had in her when she arrived,” holding up the butt plug.
Then whispering in my ear he said, “Do you want my big, cock sissy?”
As he teased my pussy with it, I moaned and said, “Yes. Yes, I want your cock! Please Sir, fuck me with your big cock!”
As he forced it in he held my hips and fucked me hard. Then grabbing my clit he rubbed and stroked it till I came all over my stockings. Mr. Smith fucked me hard, until he came in my ass. Then grabbing the camera he filmed the cum leaking out. The cuffs were then removed and he sat in his chair.
“Suck my cock again Maggie.”
I did as I was told. I loved his huge cock.
As I did he said, “Look at me.”
I looked up into his eyes and he was filming me.
“Do you like the way your boi pussy tastes on my cock?”
I did the best I could with a mouth full of cock to say yes. I sucked his cock for what seemed like an hour until he came in my mouth. All on film. I was then allowed to get cleaned up and told to go home.
(Image Source: Moonglow)