CrossdressingChapter 11 of 12Ongoing

Blackmailed by Mr. B

Blackmailed by Mr. B Ch. 10

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Blackmailed by Mr. B Ch. 10

Note from the author: Sorry for the delay between chapters, I am trying to write faster. I am responding to feedback messages now, so be sure to include your email if you want me to reply! I love talking to readers and other authors!

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

"That's a lot of cum" Maria said, looking at the panties. We were sitting on her bed after school, and I was trying my best to not look nervous.

"Yeah... I was thinking of you." I said sheepishly.

The panties were still wet, due to the plastic sandwich bag they had been in. I watched in horror as she sniffed the glob of cum in them, and giggled.

"Wow, that's so hot." she said, "I made you that turned on?"

I shifted uncomfortably. I didn't like lying, but it was called for if I had any hope of having a relationship with her. Mr. B had shown me the night before that I was firmly his until he decided he was done with me. I would just have to live a double life until he let me go.

"Uh... yeah" I stuttered out, not sounding confident at all, "It was that picture you sent me."

"Really?" she bit her lip and smiled at me, "You know, my parents aren't home for at least a couple hours..." her hand found my thigh and moved up it to my crotch.

She giggled, and pulled it away quickly, standing up and bouncing across the room to the door. I watched as her bubble butt bounced up and down. For such a petite young woman, Maria's lower half was thick. This, in combination with her tight core and smaller breasts, made me weak every time I saw her.

"I'm gonna get changed... do me a favour, get naked and lie on the bed." she grinned as she said this in a demanding tone.

My heart was pumping. After all the kinky things I had done, for some reason being naked in front of this girl terrified me. I liked her, sure that was true, but I still cared for Sonya too. I knew deep down that the true fear came from somewhere else. I pulled off my pants and boxers first, and then my socks and finally, my shirt. I sat on the bed for a moment and was about to lay down when my eyes became fixated on something. Maria's dresser. The top drawer was open, revealing a space stuffed with panties of all kinds. I listened for her footsteps and once I was sure she was downstairs, I bolted across the room and pulled the drawer out further.

The front of the drawer had bikini cut, and tame looking underwear but at the back, I saw the more interesting stuff. I pulled out a red lacy thong and saw there was a split on the bottom that would line up with her vagina, and wondered if she had used them as intended before. Digging deeper, at the very back, there was a sock stuffed with something. I reached in with a finger and fished out a white pair of slimmer bikini cut panties with a pink heart on the front saying Daddy's Girl. I turned them around and saw these also had a hole, only it wasn't on the crotch, it was positioned at the back, and roughly 2 and a half inches in diameter.

I heard footsteps bounding up the stairs and panicked. I slammed the drawer shut and ran back to the bed. As I did I threw down the panties and kicked my shirt over them and pushed my clothes under the bed with my foot. Just as I laid down, the door swung open and Maria entered. She was dressed differently from when she left... very differently. She was in a slutty french made outfit that was clearly too small, even for her smaller frame. The skirt was short enough that I could see as she closed the door she wasn't wearing underwear. She turned to me with a grin and walked to the bed slowly holding something in her hand: a can of whipped cream.

"Bonjour monsieur, I am here to do some cleaning. I hear you are a very dirty boy." she said with a fake french accent.

I was laying back with my hands over the thing Mr. B had called my "clit" so many times before. My heart was pumping, but I tried to look calm. She held the can of whip cream up and spoke again,

"Move your hands away please monsieur" she demanded, and I did as she asked, my face growing warm with embarrassment.

The last time she was in close proximity to my penis, it didn't react how either of us had hoped. Despite my excitement and desire to please her, I was terrified it would happen again. I thought back to Mr. B telling me I wouldn't need the chastity cage eventually, and wondered if this was what he meant. My worries were temporarily suspended as I heard a sharp sound and felt cold whipped cream spraying over my groin, covering everything completely. She looked at me excitedly before her smile faded slightly and she dropped the accent.

"Are you okay? You look overwhelmed?" her eyebrows furrowed with concern.

"Yeah, I'm great... you're just so... sexy. It caught me off guard." I stammered out.

Her smile returned in an instant.

"Tres bien!" she said, "Now Monsieur, you have been very messy... I will clean."

She hopped up on the bed, but instead of finding her between my legs, she swung her leg over my chest and straddled me, facing my feet. I felt something hot and wet on my chest, and as she bent forward, I watched as her pussy, dark pink and swollen, pulled away from my bare skin, leaving strands of thick clear fluid connected. I felt her tongue push through the whipped cream and caress the tip of my penis gently and then follow it down the shaft to my balls and then back again. Her lips tightened around the lead and her tongue swirled as she sucked on it like a lollipop.

"Mmmmmhh" she moaned as she worked.

What followed was what most men would have probably considered the best blowjob of their life. As it was happening I had the perfect view of her throbbing pussy and tight asshole, resembline a cute, fleshy, balloon knot. Her scent invaded my nostrils as she worked. It was gentle but pronounced, somehow sweet and savoury at the same time. By the time she came up for air, I was drooling profusely. She had dropped the accent again, only this time, her tone was more that of annoyed disappointment.

"Seriously? Not even a little hard? Do you even want to hook up with me?" she was still facing away as she spoke.

"Yes! Really, I don't know what's going on... I think maybe just nerves?" I explained desperately.

"Fine, fuck it. I'm getting mine at least." With that, she bent slightly forward and without warning jammed her pussy into my face.

It was soft, yet firm, and not only was it warm, it was hot. I could feel the blood pumping as she slid it across my chin up to my nose and back again. She ground on my face for a few seconds, and then again, in an annoyed tone without a fun french accent, she spoke.

"Stick your tongue out, dumby." she almost sounded angry.

I did, forgetting that I had been salivating so much. Saliva was pushed from my mouth and was dragged by her pussy across my face as she continued grinding. She let out a higher pitched moan and spoke again, this time the accent was back.

"Oui monsieur, I love it sloppy, keep my pussy nice and wet until I cum."

It went on like this, she used my mouth, tongue and face for the next ten minutes, moaning and gasping before she spoke again, with her natural voice, although raspier and pleasure filled.

"Good boy... keep your tongue straight out, I'm gonna cum soon..." I stuck it straight out of my mouth and she pushed her pussy down so it rubbed her clit before penetrating inside her, "Just like that... just like that, let me fuck your face... be my good little sex toy... oh fuck.... yesssss... i'm gonna fucking cum on your face..."

She suddenly jerked forward slightly and pushed down and my tongue was pushed deep inside her asshole.

"Yeah baby, taste my asshole... fucking taste it bitch... fuh - cking... ta- ahhh- aste", She went wild and bounced on my tongue like that a few times and then began screaming in pleasure as liquid spurted out of her pussy into my mouth, down my chin and on my chest. Her breathing slowed and she sighed loudly.

"Fuck, that was fun." she said, "Good boy."

At this I felt my penis, still soft, and not being touched tense up. It wasn't a full orgasm, but it was still an overwhelming pleasure and enough cum to fill up a shot glass dribbled out slowly. I felt my face grow hot and flushed. She began giggling so hard, she couldn't speak for a few seconds.

"Wow... did you just... cum?" she asked.

"Uh, yeah... I think so..." I replied, dying of embarrassment.

"Well, it's a good thing I'm a maid" she said, with the french accent again, and her mouth descended on my cock, slurping the load up. Her ass tipped back down as she sat up, and her little butthole found my lips, causing her to giggle.

"Kiss it" she said, with her mouth full.

I did, and she laughed at the wet sound it made. She turned around, still straddling me. Now her pussy was pressed against my soft dick, and it was hotter than ever. She moved her face close to mine and kissed me. Her mouth was closed at first, and as her tongue pushed past my lips I opened mine to return the kiss. She pursed her lips and spurted the load she had licked up into my mouth, not giving me any time to protest. She continued kissing me for another few seconds before pulling away.

"Swallow monsieur" she said in the accent again, watching me intently until I swallowed making an audible gulping sound, "Good boy" she said tapping my nose.

She stood up and began to change into a comfortable pair of shorts and a tank top as I laid there wondering what happened. The sound of a vibration filled the air and I looked toward it. My phone was on the ground, probably after falling from my pants as I pulled them off. Maria bent over and picked it up.

"Who's Mr. B?" she asked, "He just texted you, saying 'my house, now'"

"Uhh... that's my boss... kind of, I mean... I'm working for him." I said unconvincingly.

"What do you do?" she asked, as my phone buzzed again and I prayed it wasn't anything related to the actual work I do for him.

"Uh, odd jobs, he is kind of a neighbourhood handyman... my parents know him." I said, watching in horror as her eyes moved toward my phone again.

"He says 'Your show is starting in an hour, run, don't walk'... what show is he talking about?" she asked with a confused look.

"Uh... oh it's-" before I could say a word, the sound of the front door opening cascaded through the house.

"Oh shit... my mom is home. Get dressed, quick, I'll distract her. When we go into the backyard leave through the front door."

She threw me my phone and bounced out of the room and I heard her asking her mom about the pool heater as I quickly put on my clothes. It was a lucky break as I had no idea how I was going to finish my last sentence. I was able to sneak out the front as she had directed me, and began jogging to Mr. B's house. I wasn't exactly sure what he meant by "show" but I suspected it had something to do with a webcam.

As soon as I entered, I was handed a water bottle and an outfit and told to strip. He spread my cheeks roughly, and spat on my hole, before sticking his forefinger all the way in. His other hand grabbed my throat firmly from behind.

"Are you ready to be my bitch again today?" he asked.

I didn't answer. He finger fucked me roughly for a few seconds and then pulled it out. He pulled his finger out and held it to my face.

"Yes" I said, and then moving my pursed lips over his finger and allowing it inside my mouth. I sucked for a moment and he pulled it out with a cartoonish "pop".

He collected my clothes and then handed me a water bottle before sending me to the bathroom to change. I was thirsty from the run so I chugged it entirely without a second thought. I closed the bathroom door behind me and looked at the outfit. It was a black crop top tee shirt that said "fuck toy" in pastel letter, fishnet stockings, and a black latex skirt too short to cover anything. There was a picture taped to the mirror, and I did my best to copy the makeup and hairstyle using the supplies he left out for me. I created a side part in my shoulder length hair using a bobby pin with a black bow on the counter. There was a bottle of lube as well, and I helped myself to some, applying it around and inside my hole, just to be ready. As I was about to leave I saw something on the counter. A chastity cage next to a small lock. I was puzzled at first, and then accepted that as always, my confusion wasn't really relevant. I popped the cage on, and locked it in place.

I noticed a light on in a bedroom at the end of the hall and I walked toward it and pushed the door open more. There was a king sized bed against one wall, and several lights set up around it. A large screen TV was facing it with a webcam affixed on the top. Below was a small table with a sex machine firmly attached and aimed toward the bed. An eight inch dildo was attached to it, ready to go. I saw another camera on a tripod on the one side of the TV to capture an alternate angle, and yet another clamped onto an overhead light fixture looking down at the bed. The room was dark in tone with the walls a dark purple and the bed spread a deep red. A shelf hung above it, with various sex toys positioned on it in full view.

"Here" he said looking up from adjusting one of the lights, "Drink this"

It was another water bottle. Being thirsty, I took a few gulps before I began to feel suspicious of it. I looked at it cautiously and he laughed.

"Nothing about this show is going to go differently if you don't drink it. It's a matter of whether you want it to go easier or not."

I resigned myself to the evening ahead and finished the bottle. There was a warmth growing in my chest and face and I realized the first bottle had already dosed me with whatever it was. I was feeling relaxed, which only bothered me slightly, due to the intoxicant in my system. Earlier with Maria, my fantasies were coming true and I was a ball of anxiety. It was unfair that here, with this monster of a man, about to do things that would surely fill me with regret, I was feeling calm and collected. I laid back on the bed, against a big body pillow and Mr. B threw me a chastity cage. I put it on without a second thought, locking it and tossing him back the key.

"Showtime" he said, and hit a button on a remote before sitting down in a chair out of view facing a laptop.

The lights dimmed slightly, and changed colors and the TV screen lit up. I was there on the screen in a box that took up a quarter of it, the rest was a chat log. Above the chat in big bold writing it said "LIVE: 498 viewers". Almost five hundred people were waiting just to see me. Below my picture, there was another window, just a notepad app. Typing appeared in it as Mr. B tapped at his keys.

It read: 'Give them a wave and blow them a kiss'

I smiled shyly, and did as he said. The chat exploded.

"she's finally on!"

"let's see that hole slut"

"where's your daddy?"

"show us your feet"

"how many guys have u fucked?"

It was overwhelming.

A poll popped up in the chat:

What should Candy use first?

1. Plug

2. Beads

3. Dildo

4. Fuck machine

The response was fast and not unexpected. I pulled myself forward toward the edge of the bed, lining myself up with the fuck machine. The notepad began filling with words as Mr. B typed quickly.

'other way, hang your head off the bed'

I turned around and hung my head backwards off the bed, the dildo inches from my mouth. Big bold red letters appeared in the chat but it was difficult to read them. I opened my mouth and the dildo pushed forward slowly stopping at the back of my throat. I could still breathe but the depth the head of the dildo stalled at gently probed my gag reflex. I was able to fight the urge gag, but felt my salivary glands begin working overtime. The sound of a coin dropping rang out from the TV and the dildo withdrew slowly until it was a couple inches from my face and then pushed back in again. It began repeating this motion and rhythm. Strands of thick saliva connected my lips to the dildo each time it left my mouth. Soon more coins sounded and as they did, the dildo began picking up speed. Although I couldn't make out the complete sentence the three words I was able to make out helped explain this phenomenon: 'tip' and 'speed'. The third word was the one that worried me: 'depth'.

Within a few minutes, and many coin sounds, the dildo was moving at a speed that would be described as hardcore fucking. A new sound rang out, this one recognizable as a cash register. The dildo slowed and pulled out. A robotic voice counted down slowly,

"3... 2... 1...."

On one, it pushed in slowly, further than before, almost 'popping' past my gag reflex deep into my throat. In an instant, it began fucking my throat at a high speed for around 15 thrusts before pulling back out leaving me wide eyed gasping for air. Not even 5 seconds later, the robotic voice rang out again,

"3... 2... 1..." and the dildo moved forward slowly, entering my mouth as I was mid gasp, and sliding inches deep in my throat.

It fucked my face vigorously like this for three more rounds, until thick saliva was pouring down my face each time it gave me a chance to breathe. On the fourth round, it pulled out and as I coughed gently, a big spit bubble formed on my lips. The robotic voice counted down, only this time, when the dong pushed past my throat hole, I felt a wave of pleasure. My knees pulled up to my chest and a small amount of cum dribbled from my caged clit. I moaned with the dildo deep in my throat, which caused me to gag as it fucked my face. When it pulled out it stayed out this time and I was able to catch my breath.

My eyes were watering so badly that I was unable to see the screen but I could make out by the shape of the words in the chat box that there was another poll. Luckily, Mr. B had made the notepad text large and bold so I was able to read his instructions.

'get on your back and spread your legs.'

I moved back into the position I had originally planned for, on my back with my knees bent and spread at the edge of the bed. The dildo, now slimy with my spit, pushed int my hole slowly until the thick head popped past my sphincter. I let out a squeak as it did, surprised that with how much action my ass had seen recently, it still felt tight. The robotic voice began counting down as my eyes adjusted to the poll that was pinned in chat alongside the voting record:

"How deep and fast is she getting fucked?"

1. halfway in, 2 inch thrust, 100 BPM (21 votes)

2. all the way in, 3 inch thrust, 120 BPM (34 votes)

3. half way in, 4 inch thrust, 140 BPM (43 votes)

4. all the way in, 7 inch thrust, 200 BPM (406 votes)

By the time I read the fourth option, the fuck machine started up and the dildo was sawing in and out of my ass with extreme speed. My mouth opened wide and I let out a high-pitched involuntary moan. My p-spot was being smashed over and over again at a rate of over three times a second, and the sensation was overwhelming. Every time I thought I was starting to handle it, a sudden jolt of pleasure would cause me to gasp and go wide eyed again. I was able to steal quick glances at the screen once in a while and saw a username I recognized.

cutegrlxox: yessss girl, take that fucking dildo... did anyone see her spurt when her throat got filled?? bet she explodes out of that cage soon ;D

The dildo kept going for three minutes before I could feel the lube and spit starting to get sticky. Almost as if on cue, another poll popped up, although the pleasure was building to a point it was so strong, it took 30 seconds before I could focus enough to read it. The votes had already decided the outcome.

"Does she need a break?"

1. No, fuck her until she cums. (798 votes)

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