Blackmailed by Mr. B Ch. 02

ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.

The next day I met Sonya at the mall after school at her behest. She was picking out a prom dress and thought I might be more help than her single father. We walked from store to store and finally after much longer than I had hoped she settled on one. We went and got a bite to eat in the food court and as we were eating I heard a voice behind me.

"Fancy seeing you here!" it said as I cringed.

I turned my head and the man was staring right into my eyes from three feet away.

"Mr. Brown!" Sonya said excitedly.

"Hi Sonya, how's your father?"

Oh yes. Her father's old business partner. I felt faint and their conversation zipped by me. She showed him her new dress, asked what he had been up to, introduced me as her friend, I just sat there trying to hide my shame and anxiety.

"Is this your date to the prom, Sonya?" he asked.

Sonya laughed. That's right, giggled.

"Oh no Mr.B, just a friend, I don't have a date yet."

Yet. Just a friend. Oh boy.

"Well I have to be going Sonya. I have an important meeting at 7. Nobody would want to be late to this meeting." He said the last line while looking directly at me.

We finished eating and I subtly checked my grindr and saw that he had indeed messaged me.

*7, my house, don't be late ;)*

I made up an excuse and left but didn't have enough time to stop at home to grab the clothes. I figured he didn't care about me being feminine anyway so I didn't think it was a big deal. Turns out it was.

"Where's your clothes? I want a whore, not some guy." he commented.

"Sorry, I didn't have time." I said hoping he would send me away.

"No it's fine, I've got some stuff. Go in the bathroom, we are going to shave everything, you should be smooth for me from now on."

The next 45 minutes he shaved, waxed, and epilated, until all hairs on my body below my eyebrows until I looked like I hadn't hit puberty yet. The only thing he left was a small tuft just above my crotch. It was a humiliating experience, on my hands and knees in his bath tub while he took away my masculinity strand by strand. After came my first ever enema, that he embarrassingly guided me through. I finished with a shower and afterwards moisturized at his behest. He provided me with thigh high athletic socks, white and pink running shoes, and a school spirit shirt from my school, cropped to show my midriff. No pants or shorts, leaving my nether regions totally exposed.

"You like Sonya don't you?" he said as I dressed. It was more of a comment than a question.

"N-no. Definitely not. We're just friends." I said desperately wanting to avoid the subject as I laced up the shoes over the stockings.

"I saw your face when she said that same thing at the mall. I wonder what she'd say if she saw you now?"

I felt my face get red and flush with embarrassment and anger as I pulled on the shirt.

"Do I get a skirt or underwear?" I asked, in a tone too similar to that of a petulant teenage girl.

He lumbered toward me with something pink and plastic in his hand and began fondling with it around my cock. I felt a lock click and he stood back.

"This handy device will keep your cock soft. Eventually it'll be trained and you won't even need it." he explained.

Won't even need it. The words echoed in my head. Did he mean I would be able to stop myself from getting hard or that it would become an impossibility?

"Follow me, your parents will expect you home soon and I need to get off still."

I followed him reluctantly into his bedroom. He had me lay on my back and threw me the blindfold.

"No way, you're just going to film me again." I refused and threw it back to him.

"You're right, let's cut the bull shit." He disrobed and pulled out a camcorder from a dresser and hit the record button.

His cock was mostly erect and he walked toward the end of the bed reaching for my foot and pulling me to the edge.

"What the fuck. I'm not. Letting you record me" I shouted, covering my face.

"Okay, I'm sure Sonya would be delighted to get the first copy of your porn debut." he said as he spat on his hand and started lubing up his cock, not even hesitating.

I didn't say anything to that. I looked to one side in defiance, intent on at least making it boring for him.

"If you want any extra lube on your pussy that'll be up to you bitch. Act now or forever hold your peace."

I brought a hand to my mouth and spat in it before bringing it to my ass and rubbing it in. His cock was working it's way in me as soon as I brought my hand away and I instinctively looked up, directly at the camera lense. He fucked me hard and fast catching me off guard and I moaned in a mixture of discomfort and unwanted pleasure. Something felt good, but I knew it was a physiological response. I wasn't gay.

"Is that daddy's dick fucking you?" he asked while he pushed in and out.

I ignored him, half intentionally, half because the situation was so overwhelming.

He thrust in all the way and left it there, grabbing my face by the chin roughly.

"Is. That. Daddy's. Dick. Inside. You?"

he asked again.

"Yes." I replied meekly.

He didn't move an inch.

"Do you like it?" he asked, still not moving.

The red camera light was on, taunting me. Pushing me to rebel.

"No" I said, anger in my voice.

The camera light went off.

"Fine"

He pulled out all the way, leaving me feeling stretched and empty. He left the room promptly and I laid there, legs up and bent on my back waiting. After 5 minutes when I didn't hear him return I stood up and went looking. He was in his study sitting at his computer chair in front of his two screens. On one he was drafting an email, while on the other he appeared to be using video editing software. The camera was plugged in via a USB cord. I looked closer at the email and saw it was addressed to Sonya.

"What are you doing, stop it!" I yelled.

He ignored me and began attaching the video file. It was large and the progress bar moved slowly.

"No, I don't think I will. I gave you a chance but it looks like you're more trouble than you're worth." he responded coldly.

"Please, please I'll do it, I'll do what you want, I'll say what you want!"

"Too little too late" he reaffirmed as the progress bar reached a quarter full.

"Please don't send it to her, please. I'll do anything. Anything!" I pleaded again.

He ignored me again, and as the progress bar moved just past halfway I knew I had to do something. I decided in that moment if I was going to get through this I'd have to play a role just like in a school play. I had to become what he wanted so he wouldn't fuck my life up. I saw his dick was still mostly hard so I wedged between him and the monitors and reached down and grabbed him, aligning him with my hole. I sat down, impaling myself on it and felt his hands grab my hips and help guide me down.

"I love daddy's dick in me" I said confidently while leaning back taking all of it in.

It was a stretch for sure, but oddly the pain wasn't really there this time. The way it fit inside me felt good. Not necessarily pleasurable although on some level it was satisfying, but more like it just fit well. He pushed my back forward again and guided me up and down a few times helping me find a rhythm. I rode him like a pornstar, grinding, bucking, gyrating all over his dick. I acted like I was having the time of my life moaning and crying out.

At one point I turned him on so much he stood up, still inside me and started fucking me from behind roughly. As he did something deep inside me started feeling weird. With each thrust I had a sudden feeling of having to pee but I didn't think I had to.

"Fuck yes daddy, fuck your little whore!" I shouted and moaned.

"Do you want Daddy's cum in your pussy?" he asked as he fucked me double time.

The peeing feeling intensified and I began to find instances of pleasure in it.

"Yes dah-ddy!" I squeaked out.

His faster and harder fucking was doing something to me. I was now convinced that the feeling was not me having to pee, but something else entirely. I let my muscles relax and sure enough my dick released a dribble of pre cum but no pee. My mind set was now not unlike the one usually reserved for masturbation. My body and mind were working toward cumming. At this point it was too late to turn back and somehow even he knew it.

"You gonna cum while daddy fills you up?" he asked, hypothetically as we both knew the answer.

He pulled me up on my feet as I felt him explode inside me and I almost blacked out as I had the most explosive orgasm of my life. As it began to dissipate I looked down and there was a puddle of cum on the floor under me. The cage was still dripping in gobs and I felt that there was still lots trapped inside. He let go of me and I felt his cock slip out and as I stepped forward I felt a warm trickle down my leg. Looking down, I saw cum dribbling onto the floor, joining the mess I had already made. I clenched tightly to prevent any more from escaping my weakened hole.

"Good girl, now come clean daddy off" I heard him say behind me.

The illusion was wearing off at this point and the post orgasm sobering feeling set in. I saw the USB cord on the desk, no longer attached to a camera and my heart sank. I turned around, unsteady in the pink running shoes and saw him sitting back in the chair, camera in hand, dick still a little swollen and slick with cum. Thinking about the email, I attempted to maintain my composure and stepped carefully over the puddle, finding my way to my knees.

"Do you want to taste yourself on daddy's dick sweetheart?" he challenge me.

I looked up at the red light again, once more facing a decision, this time I chose to submit.

"Yes daddy, let me taste my ass on your dick. I want to clean you up."

And clean him up, I did. I had to fight the urge to gag as I made my first long lick up his shaft. The taste and smell weren't that bad, especially thanks to the enema, it was more the idea of it. As I licked and sucked I grew more relaxed and unfocused. Eventually I began trying to deepthroat him and he leaned forward and began spanking me with one hand. My ass muscles released and the cum left inside me came flowing out, joining the already substantial cum cocktail there.

"Oh no, looks like babygirl made a mess" he announced and pulled me off his cock.

I looked up at the camera in a daze. He stood up and stood beside the puddle aiming the camera down at me.

"Slurp it all up honey" he said as he beckoned at the puddle, "and show me it all in your mouth"

I looked at the e-mail behind him nervously. The video was attached, all it would take was one button. He saw me looking and grinned. He used his free hand to discard the draft and then beckoned once more. I nodded, defeated. Down on all fours I pressed my lips into the warm puddle and slurped until my mouth was full. It became difficult as past a certain point as I was trying to slurp, cum would be falling out too but eventually most of it was in my mouth. I turned and showed him, head leaning back to not spill any.

"Swallow baby, if you want to."

He wasn't giving me a real choice, I knew what he expected and I swallowed. That was it. He ended the recording and sent me on my way, reaking of cum. He didn't even let me get dressed, made me throw on my sweats over the stockings and my sweater over the shirt. I left the shoes there, they would be hard to explain to my parents.

I got home without incident and made it up to my room after a quick goodnight to my parents. As I peeled the stockings and shirt off I noticed he had sent me a message. It included a makeup tutorial and a curling iron tutorial and I watched them begrudgingly knowing they would come in handy later. Again my night finished with a long shower, although I still didn't feel clean after it. I fell asleep wondering what was in store for me the next day.