Blackmailed by Mr. B Ch. 03

A note to readers: The story will start to get more extreme from here on (think facial abuse or assylum type content). If you aren't into that, it's best to stick with the first two.

ATT: 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 went by normally for the most part. Prom was approaching fast and I knew if I was going to ask Sonya, I'd have to do it soon. She was pretty, and not unpopular, definitely not a girl that would go alone. I decided to ask on our walk home, that is, until I got a message during morning announcements.

*Outside, now*

Luckily my homeroom teacher wasn't a tyrant and had no issue excusing me for a moment. My heart beat fast as I ran to the entrance. Sure enough he was parked there, in front of the school. I walked to the car and bent over to talk to him.

"Get in." he said bluntly before I could speak.

"I have class, I ca-" I protested.

"Get. In." he repeated.

I didn't have much choice and I certainly didn't want to cause a scene. I entered the car and away we went. He handed me a water bottle and told me to drink. I was a little suspicious but it appeared to be sealed so I shrugged and went along with it. He didn't live far from Sonya and I so I was a little concerned when we went the opposite direction. It didn't take long to realize that we were leaving my small town behind and heading into the big city. I called my school and signed myself out for the day, something I could do as an eighteen years old. I understood at this point he had no intentions of getting me back for second period.

When I finished the water bottle he handed me another and encouraged me to drink it. We arrived after 30 minutes of driving and turned into a parking garage. He hurried me into an elevator and up to what appeared to be the top floor penthouse. He led me into a bedroom where there were clothes laid out on the bed as well as another water bottle. It was a cocktail dress, silk panties, a matching bra, stockings, and a garter belt. Beside them was a curling iron and a makeup bag. In front of the bed on the floor was a pair of classy looking high heels. After a half hour of working on my hair and makeup I got everything on and walked out of the room. I found him in a large living room with two story high windows overlooking the city and modern decor. There was a red couch and surrounding it three tripods topped with cameras.

"Perfect sweetheart, look at that hair, such a pretty little bitch" he commented as I entered.

"Uhhh, do you think we could leave the cameras out of this... You have enough to blackmail me with." I reasoned.

"I'm not recording you for blackmail, bitch, don't be stupid"

"Then why?" I inquired.

"None of your business. Your business is doing as I say, got it?" he retorted.

"Yes" I answered quietly.

"Great. Now sit on the fucking couch and read the teleprompter when I tell you to. It'll be question and answer, so make sure you ignore my lines and read whatever is written in pink. Try to sound like you want to be here, at least as much as you can. You refuse one fucking thing and Sonya gets every video I made of you."

I was very aware that this wasn't going to be an easy afternoon for me. The three water bottles were starting to make a reappearance and I elected to give him a heads up.

"Where is the bathroom?" I asked and he shot me an impatient look.

"Hold it."

"I don't think I can... I will be quick I promise." I pleaded.

"I don't care how quick you'll be, we aren't here to waste my time. Hold it."

He said this while stifling a grin and I suspected he gave me the water on purpose just to make everything harder on me.

I sat on the couch and saw that the middle camera had a built in teleprompter. At the moment the text read *Standby*. He fiddled with the camera views and checked inside a bag on a small table next to the camera before looking up at me.

"Action!" He said as words appeared.

"Okay honey, what's your name?"

"Candy" I read out loud.

"How old are you Candy?"

"18" I responded. It would be one of the few accurate answers I'd give.

"What brings you in to Gurl Test auditions?"

"Uh- well I watched the videos online and I knew it was something I wanted to do" I didn't like where this was going.

"You look good for a boy. Very lady like."

"Thank you, you're so sweet." I read.

"Except for that clit. Do you always keep it locked up tight?" he asked.

"Yeah, it's too-" I began to read the lines but he cut me off.

"Show it to us."

It wasn't written on the teleprompter but who was I to argue. I stood and pulled the dress up enough to expose my caged "clit" as he called it. He waved me back down and I start again, my face undoubtedly flushed with embarrassment.

"It's too small and ugly for any girls so I just ignore it" I continued my line, chipping away at my own pride.

"I'm not surprised. I feel bad for the girl that took your virginity."

I really didn't want to read the next sentence. It was clear now that this script was written with me in mind. He was trying to tear me down and hurt me. Knowing there was no other choice I continued the charade.

"I've never been with a girl like that" I said, trying to be bubbly but voice wavering slightly anticipating having to read the next sentences.

"Really? You're a virgin? You don't like girls?"

"Well I'm not a virgin. I really like one girl, my neighbour. I was hoping to take her to prom and lose our virginity together."

"How cute, but you lost yours already? How'd that happen?"

"I let her dad's friend fuck me a couple days ago"

"And now you're already doing porn. You're a fucking whore aren't you?"

"Yes... I am." I struggled with how true these words felt.

"It's okay, she's probably gonna get some football player's dick on prom night anyway."

My eyes were tearing up and I fought the urge to cry with everything I had. At this point I was on autopilot, the teleprompter was king.

"So you know how it works then? You make it 60 minutes and you get the prize. Anything goes. Just say 'Fuck me up daddy' when you're ready"

Prize? What prize was he talking about?

"Fuck me up daddy." I read without even thinking.

He reached into the bag and pulled out a long clear double sided dildo and tossed it to me. I hesitated and looked at it as if it was some piece of alien technology.

"Get your fucking legs up on the couch bitch and pull your ass out." he snapped.

The monitor displayed in green text *Do as you're told*

His sudden aggression caused me to overcompensate and I clumsily pulled my legs up on the couch. I pulled up the tight dress until it rode up to my waist and he slapped my knee twice before I understood he wanted me to spread my legs more. My asshole was now exposed to the camera and I had to take a deep breath to calm myself fully.

He held his hand out to me.

"Spit." he ordered.

I did and he immediately brought his hand down and rubbed it into my hole. He brought his hand back up and slapped me, catching me off guard. My mouth hung open and the sting from the slap paralyzed me. He obviously took this as an opportunity, grabbing the double ended dildo and shoving it into my open mouth. He fucked my mouth with the rubber dong violently, occasionally pulling it out to slap my face. He thrust it in deep, causing me to gag and push his arm back. I tried. To catch my breath but he used that as an opportunity to force it in again, farther this time, causing me to gag more as spit and phlegm bubbled out of the sides of my mouth.

"That's better" he said as he scooped some with his hand and rubbed it into my asshole.

He took the dildo out of my mouth and brought it up to my hole and pushed it in unceremoniously. A gasping squeal came out of my mouth as the toy opened up my tender asshole and pushed inside. I looked at him dumbfounded as he pushed it in and out rhythmically and felt the familiar massaging sensation inside myself. He abruptly took my hand and placed it on the dildo.

"Why am I doing all the work. Fuck your own cunt bitch" he ordered and I took over for him.

As I rammed the dildo in and out, I felt that familiar feeling of having to pee begin deep inside of me. I remembered how much water he had me drinking and decided this time it might be real. As I fucked, I let out little winces and moans naturally and unprompted as the pleasure underneath the discomfort was in fact real.

He checked his phone as it buzzed and then rolled the main camera and teleprompter backwards. He walked over to the front door and opened it, allowing two men to enter. They were his age roughly but a little more fit. They walked inside and began stripping off their clothes. There was a bald one and a Hispanic looking one and they both appeared to have thick cocks. The pleasure I was feeling subsided almost immediately and was replaced by panic as they walked over to me, rigid cocks swinging back and forth.

"I brought you some friends" he announced as the bald one came over to me and pulled my face onto his cock.

My hand hadn't moved since they walked in but thankfully the Hispanic man decided he would step in for me and began fucking me with the dildo. He sped up until he was going so fast I thought my ass was going to be pulled inside out. I moaned around the bald man's cock and he spoke.

"I think she's saying she wants a taste Felipe?"

Felipe pulled the dildo out at the same time the bald man pulled out of my mouth. The dildo was then pushed into my waiting mouth pistoning in and out repeatedly, tapping the back of my throat. I gagged violently and both men laughed at me.

The bald man sat down on the couch next to me and Felipe grabbed me by my hair and pulled me up on my feet. As I stumbled to keep my balance, he used his one hand gripping my hair, and the dildo lodged in my throat to move me in front of the other man.

"Sit on Craig's cock, come on." he guided.

I felt Craig's bulk hands guide my ass down until his cock found my hole. Together they impaled me on it, Felipe pulling my feet up on the couch so I was squatting facing the camera. Craig's cock felt massive and I reached down feeling my hole unconsciously.

"Yeah you like feeling your pussy all stretched around Daddy's cock don't you?" Craig asked.

I was holding the dildo in my mouth still, seemingly of my own volition. I pulled it out as I began to say yes but he pulled me down farther until his cock was halfway in. It seemed to be thicker the farther down I went and tears formed at the corners of my eyes.

"Bounce bitch" he ordered and I began riding him in slow shallow thrusts. The long, floppy dildo, still in my hand tapped my lips as I bounced.

At this point the full bladder feeling was there regardless of the cock being deep or not and it overwhelmed me as I moved.

Felipe motioned me to lift the dildo, still held with both my hands and I began sucking it again. As disgusting as it sounds it felt comforting, like a pacifier, and helped distract me from the massive cock filling me up.

I felt a hard slap on my ass and Craig spoke up.

"Enough of this soft shit, start riding deeper."

I let myself fall farther down with each thrust, taking his cock maybe 5 or sixth inches deep and pulling out to his head. His thick mushroom tip seemed to hold himself in me and stop me from pulling all the way off of him. His cock felt huge and I felt more stretched than I had been so far. At the end of each thrust I felt that familiar feeling of pleasure but the feeling of having to pee stopped me from letting go.

"Man you're a useless bitch. If you can't feel my pubic hair on your pathetic little ballsack within 3 seconds, Felipe is going to shove a taco up your ass."

All three men laughed at this. I didn't see any tacos lying around but I didn't want to find out if it was a joke or not. I pushed myself down until my balls were squished between his own massive sack and my cock cage and he held me there. My ass was on fire as it stretched beyond its limit.

"Damn bitch, you must really hate mexican food!" Craig remarked.

"Massage my balls bitch" he ordered.

Mr. Brown stepped forward, camcorder in hand aimed directly at me. I reached down and my hand slid across Craig's balls and my taint and began rubbing them both. It was slippery due to the long trail of saliva from my mouth, down my chest under the dress and on either side of my compartmentalized cock.

"Why don't you ask your little crush if she'll go to prom with you. Maybe she'll see this."

I pulled the dildo out of my mouth.

"I don't think so..." I said looking away from the camera

"Probably not, ask her anyway."

I didn't even try and pretend I was enjoying this. I was too overwhelmed, both physically and emotionally.

"Will you-"

"Use her name." he said coldly.

For some reason it felt like I was about to go too far. Of course the cock in my ass and the things I had already said we're arguably way worse but saying her name? That felt really wrong. But I did.

"Sonya, will you go to prom with me?"

The men all laughed and tears began dripping down my cheeks.

"Oh she's fucking cute. She still thinks she's a man. Does it make you sad to know that it won't be your cock ramming her cunt on Prom night?"he asked.

"Yes" I relented quietly.

"Don't worry, it won't be anywhere as big as Craig's. Go ahead and bounce on it. All the way up and down."

I pushed myself back up until the mushroom tip caught me and bounced back down again. I repeated this at a faster pace, building speed and sure enough the having to pee feeling was returning. The pain had subsided by a wide margin and it was slowly but surely replaced by pleasure. As I bounced hard and deep Craig complimented my new found enthusiasm.

"You can call Felipe and I on prom night if you're gonna ride us like this. We'll keep you company."

Bringing the dildo back up to my mouth and sucking I finally decided to let go and the timing couldn't have been worse.

"That's it sweetheart, pretend you're Sonya and Craig is the quarterback." Mr. Brown said loudly with a laugh. As I relaxed and gave into the pleasure pee started spraying from caged cock. The plastic prison stopped it from escaping in a steady stream and instead it seemed to spray like a thumb over a garden hose. I panicked and tried to hold it but it was a couple seconds before I was able to use my muscles to stop the flow.

"We have a squirter" Felipe announced laughing.

"You disgusting bitch!" Craig yelled and pushed me off his cock. As my ass came off his mushroom tip I yelped and shot another small stream from the sudden stretch.

"Felipe, pile drive the rest out of that dirty bitch. Craig, get the O gag." Mr. Brown directed.

Felipe jumped on the couch and pulled my ass forward and then up, taking. Both my ankles and pinning them by my head. Craig came over and wiped his slimy cock across my face and I grimaced.

"What's a matter? You were pissing everywhere a second ago. Don't you like it dirty?" he chided.

He pulled my head up and wrapped something around it letting a metal ring line up with my mouth. He forced it between my teeth and tightened the strap, leaving my mouth forced open.

As I looked up at Felipe he lined his cock up with my asshole and vegan pushing it in. There wasn't much resistance by this point but it still felt like it was being stretched. The familiar pressure built up again as he sank into me and I began to panic. As I felt his balls rest on my ass it became to much and my cock let out a small spurt of liquid. It landed more or less on my forehead and hair and as it cascaded through the air it was clear that it was piss due to its pale yellow color.

"Fuck her good Felipe" Craig said and Felipe didn't hesitate.

He began fucking me fast and deep and I put every ounce of energy into holding my Kegel muscles tight to avoid another accident. He counteracted this by angling his cock differently and I felt as it repeatedly punched my bladder from the inside. In the end it was a losing battle and with each thrust from Felipe liquid sprayed out. The first one went right across my face with a few drops landing in my mouth. The next two spurts hut me square in the nose. I felt Felipe's rough hands grab my cage and angle it and then spurt after spurt began filling my mouth as it was held open by the ring.

"Swallow bitch. Come on princess. Drink it down." Felipe said as my mouth came close to overflowing.

I made no effort to and let the excess pour down the sides of my face as I breathed through my nose.

"Come on, show everyone at home what a dirty whore you are." Mr. Brown said looming over me with a handheld camera.

I felt broken. I began swallowing and gave up trying to hold it. Pee came down in a steady stream and I drank it down as fast as it fell into my mouth. Felipe pulled out shortly after the stream ended and I was left with a perfect view of my asshole hanging over my face. It was opened still, dilated by about an inch.

"Looks like you might like Mexican food after all. Maybe we should order some tacos, her asshole still looks hungry."

I was horrified at the notion of them somehow getting an actual taco inside me and they must have seen it in my eyes.

"What's the matter? You'd probably love it you nasty cunt." Craig said.

"Check the kitchen. Let's see what we have." Felipe suggested as he held me in the same position.

Craig disappeared for a moment before returning triumphantly holding a box. I recognized it pretty quickly.

"Twinkies?" Felipe asked skeptically.

"Twinkies. I bet you $10 you can't get a Twinkie in that ass without breaking it." Craig challenged.

I began protesting but the ring gag severely inhibited my ability to communicate effectively. They laughed as I tried.

"You know what. You're on." he responded and let go of my hips letting my ass back down.

He pulled me up to my feet of the couch and I almost lost my balance again on the heels still strapped to my feet. He pushed me face down on the couch, so I was still standing but bent at the waist. My face was in a small puddle of something warm and wet and I realized it was my own piss. I felt him push into me again until he was all the way in and his balls slapped my own. He worked in short and shallow strokes, never pulling out more than an inch or two. This continued for close to five minutes as I received the usual barrage of insults.

"This bitch's ass is too tight. There's no way that Twinkie is getting in without it being mashed in there." Craig said.

"You just watch pal. I'm going to stretch this cunt out good. She's gonna gape so hard it won't even touch the sides."

I moaned out in horror as his cock massaged my prostate and they discussed ruining my asshole. I prayed that whatever damage they did wouldn't be permanent. Before I could feel too much pity for myself Felipe suddenly withdrew his cock with surprising speed. At one moment he was in to the hilt, the next he was out and his slimy head was resting on my balls.

"Getting there." Felipe said with a proud voice.

He thrust in again, holding it deep for some quick thrusts and pulled out again abruptly. He repeated this process a few more times and then pulled out and pulled me back up to my feet.

"Almost there. Get back to how you were before." he ordered and I complied, laying on the couch and raising my legs and hips up so they were angled over my head. He helped me get my legs on either side of my head and I looked up at my asshole. It didn't look so bad. It was red and a bit swollen but it was closed, which I hadn't expected considering the last time I saw it.

He pushed insider me once more repeating his deep and short thrust method and then held it.