Blackmailed by Mr. B Ch. 06

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

Upon getting home I spent at least twenty minutes brushing my teeth but somehow I could still taste both of us. As I crawled into bed I noticed he had texted me:

*You won't see me for a few days. Nothing goes in your pussy until then.*

I didn't think to much of it and certainly didn't lose any sleep over it, at least that night. The next day was wholly uneventful and after the previous evening, I was okay with that. I was in somewhat of a good mood even, considering Mr. Brown had let me leave the night before without replacing my cage. I thought it may have been an oversight but recalled him squeezing my crotch while hugging me from behind before I left.

I practically skipped home, alone that day, as Sonya had gone out with her mother after school. My parents had not come home and I decided to use that time to regain some of my manhood. I hurried to my room and booted up my computer, navigating to a popular porn site immediately. I put on the first video I saw, featuring two lesbians going at it with an army of toys. I began to fondle my cock a little bit and pull on it gently. I was almost giddy in anticipation of masturbating like a real man. It felt like a major "fuck you" to Mr. Brown which only felt right after all times he had fucked me... Literally.

It wasn't until about 5 minutes into the video I realized something was wrong. I wasn't hard. Not even a little! I skipped ahead a bit, hoping to find a more arousing part but that didn't seem to work very well. I told myself it was just the video, maybe something else would work. Three videos later, still nothing and I was starting to panic. I decided I needed to change it up and began gravitating toward the content I was trying to avoid. Shemales, trans, sissies, as I began to cycle through these videos I could feel myself get warmer and butterflies in my stomach.

It was finally on a particularly rough video of an older man and a younger crossdresser that I felt my cock become a little stiffer. The crossdresser was on her back, ankles and wrists both locked onto a horizontal bar providing the man with easy access to her asshole. She had a ballgag in her mouth and he only removed it once he had cum balls deep in her boi pussy. He had also released her ankles and wrists so she could sit up and suck his cock clean. She then laid back and jerked her tiny cock as he fingered her. When she came, he used the same hand he had been fingering her with to catch the rest of his own jizz as her orgasm caused it to squirt out of her tight hole. He brought the hand up to her face and smeared it all over. He then sat back and watched as she slowly collected the cum from her chest and ate it bit by bit.

At this point I realized my hand was no longer on my cock but slowly rubbing my hole. My cock was not even half erect and I finally accepted it wasn't going to get any farther. The feeling of being broken that I had the night before returned full force. Mr. Brown must have known it too, explaining why he didn't put the chastity cage back on me. This was what he had referenced when he first had me wear it. At a certain point I wouldn't need it, only that point had come much sooner than I thought it would.

It was two days later when I received a cryptic text from Mr. Brown in the morning that read "here cums the bride". I had no idea what it meant and tried my best not to think about it at school. I spent my lunch with Sonya, which was nice. Chad seemed to be away for a football game although you'd never know it with how much she talked about him. We walked home, like usual, and while we did she mentioned she was going on a date with him on the following Friday evening. This usually would have bothered me but as she said it something much more dire caught my attention. In my parents driveway sat Mr.Brown's car.

"Mr. Brown is at your house?" Sonya asked.

"Who?" I replied, trying to play it off.

"My dad's friend... You met him at the mall remember?" she reminded me.

She left me there, heading in to meet her sister and presumably Gwen. They had planned a girls night as her sister would be travelling for a couple months in the near future.

As I stepped inside my house warily I found Mr.Brown sitting at my kitchen table, laughing loudly along with my parents.

"Sweetie, this is Mr.Brown, he's a friend of Sonya's father." my mom said, wiping tears if laughter away.

"We are acquainted! I saw him in the mall, dress shopping." he said, and the three of them laughed again.

I went red immediately.

"I kid, I kid. He was with Sonya. She's a looker young man. Better impress that one, she'd make a great wife." he said.

My dad spoke next.

"Your mother and I are heading out to a cooking class, thanks to our new friend here. He's offered to inspect our house for mold and foundation damage. There's been a few cases in the neighborhood with the recent storms, you know."

"On the house. Any friends of Ted Miller are friends of mine" he said before turning to me, "Your mother said you'd be able to help me out. I could use an extra pair of hands."

There it was.

"Sure." I said, trying not to look shocked at the situation.

"Okay, well thanks again Mr.Brown, we appreciate everything" said my father.

My mother turned to me as they got up to leave.

"Can you believe it? His cousin runs a cooking school. It's in the city so we won't be back until late but there's leftovers in the fridge. Bye honey!"

No sooner did they leave did Mr.Brown turn to me.

"Check your phone. Shower and get your makeup on. Follow the tutorial I sent you."

After a long shower with deep cleaning, and some trial and error I was ready. My makeup was identical to the video which had the title of Elegant Bridal Makeup. It was understated but heavy on the blush and as I inspected myself in the mirror I noted how beautiful it made me look. The last thing I did was use a syringe provided to squirt lube deep inside myself. As I left the bathroom I called out to him.

"Are there any clothes for me to wear?"

"There sure is, come here." His voice came from my parents' room. I knew right away that whatever we were doing was going to be happening on their bed.

I felt a pit in my stomach and as I opened the bedroom door and something drew my attention immediately. On the bed was intricate and beautiful lacy white lingerie including garters, panties, a bra, stockings, lace gloves, and a hair band with a bow. It was much fancier than the clothes he had had me wear for him up to this point and also somewhat classier. I thought it was out of character until I saw what was hanging on the closet door next to him. A wedding dress. It barely phased me until I saw it. My parents have an old chest that sits under the wall mounted television in their bedroom. As far as I knew it contained my mother's wedding dress and a few other keepsakes. A look of horror must have come over my face as I observed that chest sitting wide open and empty.

"Wait... No... I can't..." I began, surprised that there was still some fight in me after our last rendezvous.

"You will. Get dressed." he said flatly as he set up the tripods at various angles all pointing to the bed.

Of course he hadn't bought me the lingerie or the dress, they were my mother's.

"Please... Please, please, please." I begged, getting down on my knees, tears forming in the corners of my eyes.

He ignored me and continued to work on his camera set up. I was getting desperate.

"I'll do anything... Really, anything!" I claimed.

"Anything?" he asked, a hint of challenge in his voice.

I gulped audibly.

"Okay. I'll give you another option. A choice. We can pack the dress up and forget this ever happened. It's up to you." he said, pausing his work.

"Thank you!" I said relieved, "What is it?"

"We go to a bathhouse. Right now. We don't leave until you've had at least five loads dumped in each of your holes." he offered.

It wasn't even a contest. We both knew there was only one obvious choice.

"So? What's it gonna be? We going for a drive or do you want to wear the dress?" he asked.

"I'd like to wear the dress."

Being the same size as my mother, the lingerie fit surprisingly well and though the lace felt good on my skin, it felt wrong on a deeper level.

"The dress now," he said taking a seat on the bed, "What do you think we are filming today?"

I began the arduous task of putting on the dress, careful to not rip it.

"You fucking me while I wear this." I answered flatly.

"Close" he said with a grin, "Most of the videos we have together you have needed... direction. In this one, I will be in charge at first but when we get to the bedroom you will need to fully participate. Take initiative, beg to be fucked, ask for things, thank me, talk about how much you're enjoying yourself. Be fucking filthy. But be warned, if it doesn't get nasty enough, we are going for a trip to the bathhouse tomorrow, and you are going to suck every cock we can find. Fair deal?"

"Yes sir." I said without flinching.

I knew it was no empty threat and as humiliating as this would be, I didn't want to drink a bunch of random man juice and risk an STD or something.

He helped me zip up the dress and then ordered me back downstairs where there were more cameras set up around the dining room table.

The scene started with him leaning against the table and me on my knees, prepared to suck his cock. Nothing new to me, but the feel of the dress and the lace made it seem like a big occasion.

"Here. One more thing."

As I knelt there with his cock in front of me he lowered the final piece, the veil, on my head and pulled it back as if I was a bride about to kiss my groom for the first time. I thought of my parents for a moment and the last time this dress was worn as I opened wide and took his cock in my mouth.

I made sure to occasionally pull my face off his cock to give his balls attention and this seemed to please him especially.

"Get up" he said pulling me to my feet.

I did as he requested and he turned me around, pushing me down on the table. I felt him lift up the dress, bunching it around my waist and while I stared forward I saw a camera focused on my face.

"Don't forget to play it up. Remember what happens if you don't." he whispered.

His hands roughly pulled my panties down and off and I braced for his cock, praying he had lubed up. Instead of his cock I felt his hands spread my cheeks and something wet on my hole. I felt an immediate chill deep inside me that felt like electricity in the best way. The wet thing pressed against my hole and seemed to trace around it, occasionally grazing over it. As I looked over my shoulder it plunged in me and I let out an involuntary moan. I saw him on his knees and his face buried in my ass and realized I was being tongue fucked. It didn't take long for me to follow his command to be vocal. As it turns out, a tongue in your ass tends to make you say exactly what you are thinking.

"Fuck you're eating my ass." I exclaimed, a look of surprised pleasure on my face.

A quick slap followed and his voice.

"Pussy."

"You're eating my pussy so fucking good!" I corrected myself.

I wasn't acting, it really did feel good. My asshole- or pussy- had become acclimated to abuse and although that had yielded some pleasant results, this was good too.

"Thank you for eating my pussy daddy" I breathed out, savouring the feeling as my cock pressed against the cage. I remember at some points it felt like I could cum just from his tongue alone. Eventually, as with all things, it came to an end and his face moved away.

"What would you like now?" he asked, pressing his cock against my ass crack.

"Take me upstairs and fuck me please" I said, smiling into the camera.

I led him up the stairs, holding his cock in one hand and sucking my thumb with the other absentmindedly. We entered the bedroom and he sat on the edge of the bed. I got down on my hands and knees, seductively crawling to him, working my way to his groin where I brought my face low. Taking his big ball sack into my mouth, I massaged them with my tongue, sucking gently, moaning here and there in enjoyment. His hand pulled the dress to my mid back and then found my hole, rubbing it. I spat out his balls dramatically, making sure spit was hanging from them and my lips.

"Fuck yeah daddy, finger my pussy..." I encouraged in a breathy voice.

His middle finger found my hole and pressed in with little resistance thanks to the lube already pre applied.

I pulled away from his balls and turned around, giving him better access while keeping my back arched. He added another finger and I let out a gasp of approval, backing into them right away and moaning. After a while I crawled forward slowly until his fingers slid out and couldn't longer reach me. I climbed to my feet and turned around seductively.

"Lay down please, daddy." I ordered, feeling weird about issuing him a command.

Mr. Brown laid back on the bed and I climbed up, holding my dress up high and stood over him. I lowered myself down on his face, being sure to hold my caged clit up to give him better access. His tongue invaded my pussy right away and I shivered with pleasure.

"Fuuuuuck yessssss" I sighed out as his tongue went deep inside me and pulled itself around. I held the dress up high, exposing my caged clit, dangling between the garters.

"Daddy your tongue is so fucking deep inside me!" I exclaimed, eyes scrunched shut, savouring the sensation.

His hands gripped and caressed my inner thighs as he worked my hole with his mouth. I began slowly grinding on his face and he moved his head in rhythm with me. Continuing this motion I felt my cage tighten and knew that I was building to an orgasm, albeit more slowly than I would with a cock inside me. It was then that he let out a growl sound, like a groan of approval and the reverberations of the sounds carried deep inside me via his tongue.

"Ohhhh fuck..." I said, almost losing my balance from the pleasure and bracing myself by putting one hand on the bed.

Looking down I saw my clit had begun leaking and I caught the strand before it fell to Mr.B's chest below. Without thinking I sucked my finger clean and bit my lip as his tongue continued to work its magic. It felt so good that at one point I started drooling and had to close my mouth I was salivating so much. Pretty soon I realized I could sit there for hours and had to force myself to climb off him.

"Daddy, you ate my pussy so fucking good, can I suck your cock now?"

I asked, moving between his legs and pushing my ass up for the camera at the foot of the bed. I made sure the dress wasn't blacking the view of my now very moist hole and then began work on his crotch.

I began by spitting out the saliva that had accumulated in my mouth on his partially erect cock and balls. I smiled greedily before extending my tongue out and licking all the way from under his sack up and over his balls and shaft to the tip of his cock. It glistened from the spit and a thick trail still connected his balls to my mouth. My tongue must have covered every inch of his sack as my hand pumped his wet cock above my face. I let more saliva collect in my mouth before spitting it back out on the tip of his cock. I raced to lap it all back up with my tongue, slurping the thick slime back in my mouth. After a few cycles of this I turned around, sticking my ass up and wiggling it.

"Are you ready to take my pussy daddy?" I asked teasingly.

I giggled and shuffled my body backwards and pushed myself up until I was squatting just over his cock. His head rested nicely at my hole. He lifted and bunched up the dress just enough so the cameras had a decent view of everything and I began to lower myself down. I held my breath as my pussy stretched around his cock. I understood why he had me refrain from putting anything in my hole for the past few days. He wanted me to feel as tight as possible. It almost felt like the first time he fucked me and I had to pause once his head popped in.

"It's so big, daddy..." I said with more worry in my voice than intended.

"It's okay baby girl" he said and I felt his massive hands grip where my thighs meet my hips and pull me down, "Daddy will help you"

"Ahh-ahhhhhhh" I let out a sound and my eyes went wide as I was impaled slowly on his cock.

"That's it baby" he said, "Let daddy help you."

His pubic hair bristled against my perineum as I made it all the way down and when I glanced downward I saw a long thick strand of pre-cum hanging from the tip of my very soft cock. Except it wasn't exactly soft, I could see it was stiff and almost standing at attention but it hadn't grown from its flaccid state at all. *It's a clit* I told myself in my head. As alarming as this was, I knew I needed to keep the scene going. My ass was still adjusting to the girth so I decided to buy myself some time. I reached down and gripped his ball sack gently and began rubbing them.

"Oh fuck daddy, your balls are so big. I can't wait for them to empty inside my tight little pussy." I said.

"Mmmmm you want to be a nasty whore for daddy?" he asked, his hands rubbing my legs.

"Yes Daddy" I said rubbing his balls up to where his shaft was swallowed by my hole and then to my clit. I began to slowly pull up, rubbing my so called clit as I did, surprised that it actually made it easier. On my way back down, I even spat on my hand to make the rubbing a little smoother. Eventually we worked up a good rhythm albeit not very fast. I made sure to talk as dirty as possible and found, like before, it came almost naturally.

"This is your pussy daddy. You own it!"

"I'm just a horny slut for your cock!"

"Make me regret being such a whore!"

It all blended together.

After a little while of that I began to get an anxious thought at the back of my head. He had instructed me to take the lead and be filthy and although I was taking the lead. I knew we weren't quite at the filthy level, at least by his standards. I pulled myself off suddenly and turned around on my hands and knees, once again lifting my ass high to the camera. This time I felt cold air rush in and I knew I was gaping. Without using hands I licked his cock from balls to tip and then took the head in my mouth.

"Oh yeah baby, taste your pussy." he encouraged.

After a good couple passes with my lips and tongue I pulled it out and held it against my face.

"I love tasting my pussy on daddy's cock" I said with an overdone innocent voice.

I turned around again, wiggling my ass in his direction hoping he'd understand the message. He must have because seconds later he was pushing into me, his hands gripping my midsection tight. I looked straight into the camera at the foot of the bed.

"Mmmmm daddy's cock really opened up that little hole. It was open wide when you first got off it." he told me as he began fucking me at a quickened pace.

"Uhhhh-ahhhh yeah daddy, your big cock stretched me so wide." I said, barely able to brace myself on the bed.

"You like being a nasty whore for me don't you? Being the star of my movies?" he asked.

"Yes Daddy, it makes me so horny being a naughty slut. I love being your porn star." I answered.

He picked up the pace again and I could feel him thrusting with a purpose. I felt myself getting closer too, with his forceful pounding driving me wild.

"Where do you want my cum baby?" he asked.

"In my pussy daddy! Fill me up!"

He did. I could feel each rope of cum shooting hard against my insides and felt the warmth spread. I was so close but the sudden stop of the thrusting left me reeling on the edge. As his orgasm subsided he pulled out slowly and I clenched hard to keep his cum in.