#664 - Sissy Story 13 - Blackmail

Have you ever showed yourself in a private chatroom?! by cam, of course..
never thought about to be recorded and blackmailed?!
I know, it's a deep fear and a secret fantasy of every sissy.
so, let me introduce you to this interesting story of forced feminization..
enjoy the sissy story number 13! ;))

Anna Malice


PS if you don't understand english well try to translate this story selecting your own language ;)

Blackmail

It all started as just a game. i logged into a forced feminization chat room and portrayed myself as a slave being punished by my Mistress. Saying She had instructed me to enter this room for 5 minutes and obey any command given to me. It seemed harmless and exciting. How stupid could i have been. Instantly i began getting messages for me to strip and show my ass and my face in various poses. There was one in particular who led the show. He forced me to put on lots of makeup and lingerie and pose myself as a sissy slut begging for cocks to serve. Everything was done on cam. i was naked spreading my ass and on display. After the 5 minutes were up, i left the room still getting messages from everyone who participated im my degradation. It seemed harmless and fun to portray myself and get so much attention. Then, It happened!

My E-mail popped up with a new message. i opened it and was stunned at what i saw! There were several attachments. Each one was a pic of me during the whole session and they were all clear as a bell! i had no idea you could take snap-shots like that. My face, my ass, everything i did! What the fuck! How in the hell? The message body contained the following message. "Log back on right now, and report to me BITCH!, Or else you will be more popular on the web than Pamela Anderson!" Quickly i logged in and saw Him waiting. i immediately messaged Him and asked what he wanted.

i panicked which was a major mistake! If i had only known! By the time it was over he had me back in makeup and lingerie, shave my pubs completely and lick up a load of cum. All on cam! There was nothing i could do! he threatened to spread me all over the net with the pictures he already had! Signing off he told me i was his gay fag bitch slave now and that I was to purchase a dildo and a collar by this time tomorrow night and report back to Him.

That night i could hardly sleep. Was this really happening? i kicked myself in the ass for panicking, i should have just ignored him with the pictures He first had. But at first i was afraid. Now He has even more! This was all just suppose to be a fantasy! Now, it was coming true and there was nothing i could do to stop it! Or was there? i thoroughly considered how much He had on me and where this was all going! i had to stop it. How bad could it be i thought? So i decided right then to roll the dice and ignore Him. Little did i know how wrong i was!

For the next couple of weeks i was on pins and needles and i continually surfed checking for any traces. i even went back to the chat room under a different name to see if anything was happening. After a while i figured it was over and i counted myself lucky.

The next day at work i logged on to our LAN at work to check for my normal daily info. And there it was...An E-mail from a Master!!! i froze in my seat while my heart pounded like an earthquake. He knows my real name, my work E-mail address and where i worked! i thought this couldn't get any worse til i opened it! In giant bold letters it read "AS MY GIFT TO ALL OF YOU, PLEASE ALLOW ME THE PRIVILEGE OF SUCKING EVERYONE OF YOUR COCKS. A SMILE AND A MOUTHFUL OF CUM FOR ME TO SWALLOW WILL BE MY ONLY CHARGE!"

It was sent with stationary in the background that was a collage of what appeared to be every picture He had of me!..........i went numb!.........but that wasn't all! It also had an imprint made up of our companies E-mail listing of every single person in the company! My hands went to my head and i knew now i was royally fucked. What the fuck was i to do! OH MY GOD!!!! How can i explain!!! i wasn't gay! i would be ruined. i scrolled down to see all the pictures. It was extremely long. At the very bottom in very small lettering there was a message for me which read.

"This is just a preview E-mail which is set on a 24 hour timer on my computer. It starts upon receiving a read receipt once opened. I expect you to spend this time to reflect back on the consequences for not obeying me. Have a nice life..MLC"

Oh Fuck! i was trembling! What have i done? i never thought it would come this far...OH GOD!!!! i looked at the clock which showed 10 after 7 and realized 10 minutes had passed already since i had activated the countdown to my own destruction.!

my mind was a whirlwind thinking what to do!

At first i thought, maybe if there was a power outage tomorrow morning the e-mail would fail! But then He would receive notification of the failure and just resend. Shit shit shit!!!!! my life was over!

It was then i had only one choice. i had to convince him not to do it..but how?

i had to contact him.so i immediately told my supervisor i had to go take care of some important business and i took the day off.

Driving home my mind was racing..i knew He was a gay master and i new of course what appealed to Him. It was the only shot i had! Arriving home i quickly logged on but His user id showed He was off line...Fuck!...

10:22 AM

My whole mind was in a constant state of nervousness. i had to concentrate..i had to figure a way out!

Was He really off line or had He shut me off completely from seeing Him..looking at the time i thought he must be a work...at least i hoped that was only the case.

So i set there and stared at His user id for hours just shaking in plain terror as the clock ticked on and on and on...As i sat there i tried to figure out just what i was gonna say or do...i don't have any money and never expected any in the near future...Shit...The only thing i had to offer was myself! Most importantly i needed time! Once i realized that, i stripped down naked in front of my own cam with it turned on hoping this would work. NO DICE!

i sat there still waiting and praying.

By noon time still nothing.

Then just before 1:00PM Messenger gave me the all familiar knock!

There He was! Thank God!

i was thrilled to see Him as my heart leapt in my throat! What the fuck was going on with me!

i messaged Him begging Him to stop the timer.

No answer.

Suddenly i saw He was now viewing my cam. At least i felt this was a good sign. i moved back so He could see me from head to toe. i knelt on my hands and knees as if worshiping Him. And begging. i turned around and around and made lewd gestures with my mouth and my ass. Anything i could think of! i messaged him and offered him money. i even told him i would be his personal bitch. Anything He wanted. Anything to not ruin my career! Finally i fell to my face still on my knees with hands out to the side sweating like a pig!

i was startled back to reality by an alert that went off on my computer screen above me. i looked.

It was a message from Master that read.."I prefer my bitches to beg in person." The message also contained the city He was in and a cell phone number.

Then He logged off and i was left with a decision with the clock still ticking. It was obvious He was in control and He was letting me know the way it was gonna be. If i was to get out of this it would be in person and on His terms!

Next thing i new i was setting on the plane staring out across the horizon.

The earliest flight i could get would put me in at 3 AM in the morning. That gave me about 4 hours once the plane landed.

As soon as it touched down i called..no answer!

i called again...nothing.

Looking at my watch it was goin on 4 am and i was still at the airport with nothing but a fucking number with no answer! i have never been so fucking helpless in my whole life. Here i was goin through all this begging a gay Master to let me be his bitch!!! How could i have fucked up so much! Again i was helpless. i was totally His! He had full control..i felt like his little pawn..his little toy..his little bitch! And considering the situation..i was!

At nearly 5 O'clock He finally picked up.

"Took you long enough bitch."

"i am hear Master.." i replied

i had to play for him as much as possible to figure this thing out. i started talking and He simply talked over me with an address and hung up..Shit.

After taking a cab clear across town i finally arrived at the address just before 5. The front door had a note taped to it which read "BITCHES USE THE BACK DOOR."

i quickly ran around to the back to find another note. "STRIP, AND PREPARE TO MEET YOUR NEW OWNER! YOUR OLD CLOTHES AND BELONGINGS GO IN THE LOCK BOX!"

He couldn't be serious! i stood there looking around thinking of what to do as the clock still ticked away. i knew this was only temporary. He wouldn't really throw away my clothes would He? Hopefully i could serve him well and get them back before i go home.

On the porch in front of the door was a blindfold, a ball gag and handcuffs. You've got to be fucking crazy! Staring at it there was no choice! i knew what i had to do. Shit!

Even though i knew i was not gay.the whole control thing just totally started to blow my mind. My cock started to rise as i took off my clothes and locked them inside the box beside the door. i must be fucking insane i thought to myself. i still had no choice though! my cock was now hard as a rock. i couldn't control it...there was nothing i could do. i couldn't risk disappointing Him in any way until i somehow talked Him into canceling the E-mail. One last look around and the blindfold was in place. Next came the ball gag which i hoped would not stay on for long! i wondered if i should knock before putting on the cuffs. i had to let him know i was there. i was quickly running out of time.

i knocked and put the cuffs on behind my back. With each click as it ratcheted shut i trembled. Then i knelt there and waited for my so called "New Owner"!

i thought hard about everything that had just transpired. With in a 24 hour period i went from a hard working respected business man to a but naked and bound and gagged slave on my knees at a complete strangers back door hoping and waiting to get the opportunity to beg Him to make me His fag bitch fuck toy! And to make things worse my cock was rock hard and leaking precum on His back porch!

i waited and waited. my mind was going crazy. my whole future lied in His hands now. my wrists squirmed in the cuffs reminding me of my condition and my cock embarrassingly stood out like a flag pole!

Finally i heard the door open.

i knelt there awaiting His command but not a sound was made.

Chills went up my spine as my heart was beating like crazy. i heard the flash of a camera. i pulled tightly against my cuffs and protested as my cock was fully erect bouncing and leaking cum! What a picture that must be! i was nothing but a poor slave hoping to be used by my Master! i could feel his eyes all over my body!

His plan had worked brilliantly. i was His to do with as He pleased!

Still not a sound.

Suddenly i felt a collar being locked around my neck and a chain attached. i felt the tug of a leash. i tried to keep up on my knees as i was lead inside for quite a ways. i could feel the carpet under my knees and i heard the creek of a chair as he sat down. Still not a sound. Just the TV was all that could be heard.

i heard the typing of a key board and then His zipper. i knew what was coming and tried to get away but the chain had apparently been been connected to front of his chair he was setting in holding me in place. All i could do was stay there on my knees and tremble!

"Now you can start convincing me boi...You've got about half an hour left to try and make me cum ...if not...well lets just say you'll have plenty of practice coming up bitch!" He laughed.

A sharp tug on my leash brought me forward. i struggled against it..

"Don't waste time boi..if i so much as hear a peep of anything but slurping and moaning on my cock..I will manually send this shit you understand?"

i knew i had no choice in the matter! i had to do it!......i just thought to myself.no one will ever know.just get it over with...there is not much time! my cock was still rock hard! Why!....was this really turning me on!....No no..He obviously was getting all the wrong signs from my body.and there was nothing i could do about it.

The gag and blindfold was unbuckled and instantly replaced with His cock before i could even wet my lips or stretch my mouth.

i quickly leaned in and hungrily wrapped my lips around His glistening shaft and went to work! He had to cum and cum quickly!

God i was so ashamed and embarrassed!

With as much porn as i've seen i tried to duplicate what they do. i had to make him cum and cum fast! i moaned and moved from side to side portraying a true obsession for my task at hand. Deep...around..around...i built up enough saliva to slurp loudly on the up stroke. Twist from side to side.Moaning my enjoyment. It was the best act i could do for something that disgusted me so much. It really took total concentration. i almost could not believe it was me..the better the quicker...cmon..hurry up!


( link opens in new window )

"Not too bad for a beginner boi...you sure this is your first cock?

With a plop i with drew my drooling lips taking deep breaths "Yes Master.." my neck and mouth was beginning to get sore. i hungrily moaned as i sank back to my task. With my lips hard at work i glanced over at the screen.only 20 minutes remained! i sped up faster and faster. i could not believe He was showing no sign at all of pleasure...this would make me blow my load a long time ago!

i kept total suction and went as fast as my neck would allow!! The sweat began to poor. i labored long and hard..my moans and squeals were no longer fake.i couldn't think of anything more to do! Finally i began to see a twinge in His face...YES..i was getting somewhere.finally!!! i could barely make out the counter on the screen..i believe it was 12 minutes or so..i didn't dare stop though..i had Him on the ropes! Surely it wouldn't be much longer..

Faster...Faster..and Faster..sucking harder and harder! i couldn't picture my fist doing a better job. my tongue pressed under His shaft...i was moaning loudly..tightly...

i felt His hands grab hold of my head as He suddenly buckled and rammed His cock straight down my throat! i felt his body spasm as streams flooded my throat. my arms flew up and back pulling tightly against my cuffs. A loud moan came from His mouth as my sweaty face and hair soaked His crotch. He held me there as i could not breath at all with His cock blocking my airway. i panicked and felt weak and about to pass out. Then my head was yanked back as He was still shooting stream after stream of cum all over my face! It didn't matter to me..i was trying desperately to catch my breath back. Finally His erupting geyser subsided as i realized i had finally accomplished my first task! The counter read 00:03:21. i had only 3 minutes left. i tried to talk but i couldn't hardly make a sound. Damnit..i kept trying to slow my gasping as i incoherently began to beg!

Ma.Ma.s..ter..(gasping)..p.p..please..d..d..don't..send..i.i.will do ...(gasp)...

Any..thing..j..just d..don't do this..my breathing began to finally slow down...

"Exactly what do you have in mind boi?" He asked.

00:02:31

"i need...time..(big breath)..Master." i answered

"Time for what bitch?

i thought of anything i could to get him to stop the timer..

"Time to prepare.."

"For what?"

"For becoming yours Master, please stop it..please"

From the looks of it I would say you already are bitch!" He replied.

00:01:40

i stared at the few fleeting seconds left of my old life as the cum dripped from my face and landed on my lap and ran to the floor below. It was obvious He was correct. It was my last straw..

"But..I can offer you something more Master.." i said

"Oh yea, like what?"

00:01: 02

It was the only thing i could think of that could possibly buy me more time.

"my retirement Master..i have only 3 years left..(taking a breath)..then my pay will start the day after, every month for the rest of my life.."

Without thinking i was instinctively licking the outside of my mouth as it continued to drop from my face..

"hmmmm...how much we talking about here boi?" He asked

At last a small glimmer of hope came with His very question showing He was actually interested.

00:00:43

i looked back from Him to the timer..then back..

"After taxes it would be at least a thousand a month." i said as the timer kept goin..

He smiled.." So my new bitch comes with benefits...hmmm...let me think about it."

Staring back from Him to the screen..i stammered "M..M..Master.the timer.you have to stop it or i will loose my career and it will all be over.please!!"

"Shut up bitch.I'm thinking.." He shoved the gag back in place and buckled it tight. "one more word and I'll send it manually..so shut the fuck up!"

i didn't dare make a sound.

And there it was...my last plea..I watched the numbers click down..20.19..18.17..

There was nothing I could do but wait..hope.and pray he would take it.

10.

9..

8.

7..

6.

5.

4.

I couldn't believe it was about to happen..i strained againse my cuffs and screamed through my gag...mmmmmpHHHHHHHH!!"

3..

2..

1..

Everything stood still as the timer stopped.

0

He yanked up on my chain with a smile on His face.."your lucky boi...I didn't really send it yet..but I will if you fail to convince me your worthy of serving me.if you don't I kick your ass out and send it to every account on the fucking web!. We will talk about your proposition afterward. Now, get your ass in the shower and shave every hair on that body from the neck down..you've got 15 minutes!"

i crawled down the hall to get busy shaving. i was helpless! i still had to play my part..i couldn't figure out how to get the edge. He had me cornered!

i quickly shaved as best i could when i came out i found a bright pink nightie , handcuffs and 5 inch heels along with a cosmetic case. There was a note which read "if you intend to serve then you'll do it right..". The thought really turned me on, but the idea if being in the presence of a gay Master doing this scared the shit out of me! But it was too late now..i had no choice. i had to play this right if i was to ever get a chance to get out of this!

Looking down i watched as my fuck me pumps incased feet made their way, one in front of the other. Carrying me to hopefully find approval from my new Master! my hands cuffed behind my back after doing the best job i could in applying my thick eyeliner and mascara along with the fullest luscious most bright red lips i could do. i was the perfect vision of a twisted shemale pornstar. i could feel His eyes on me as i strode across the living room swaying from side to side. Lips parted and breathing heavily as if driven by an urge from below. With his legs parted in His chair and His cock on the rise, i knelt between them peering up to Him through my best wanton eyes.

"Your wish is my command Master!" i said.

He reached down with his hand along the side my face and guided my now crimson lips to his leaking shaft. i parted and took him fully. i had to impress him as much as i could.

"Slow and easy bitch..you must learn to keep it hard while worshipping it for hours and hours..this is your first lesson." he responded.

i slowed and began to seductively massage His throbbing member as best i could as He continued to direct me further.

"Look at me bitch..I want you to know the face of the very Master who's cock your worshipping, and know it well."

i stared up at him with my puppy eyes. Staring into His..looking as helpless as i can..in my hand cuffs ...on my knees...playing my part..submissiveness was my main concern. i have to appear as submissive as i could!

His precum kept coming and it began to drool out from between my perched lips. i slurped loudly with every stroke. Feeling the pulse of His member. As it increased i slowed and withdrew until it decreased then began again..i began to under stand where He was and what to do.i milked Him as much as i could ..i knew better than to make Him cum until told to do so..with my femme side coming out as i was dressed, i was really able to play the part..

i went on and on and on.for what seemed like hours..taking breaks only to retrieve Him a beer from the fridge while He watched TV and enjoyed personalized pleasure. Walking to and fro seductively with my chin now dripping with His seed....keeping Him on edge!

"Ok slut..there is only one thing left ...as He pulled me back and began to lead me by the collar downstairs.

i did my best not to stumble bent over at the waste walking in the heels with his cum dripping from my chin. I watched as His rock hard cock bounced with every step as it dripped a mixture of my saliva and His cum with every step. my virgin ass followed close behind like a sheep being taken to the slaughter. i was lost in the moment but it seamed so right. Oh God.What was happening to me! As we descended into the dark cellar..my eyes could not be deceiving me! The dim light gave way to walls covered with many devices and whips and chains and cuffs. It was fucking S&M central! i was led to some sort of pillar waste high and pushed over it. One by one thick heavy leather straps were pulled over my silk covered back and I was cinched into place. Then He began to wrap my cuffed arms with something which pulled them so tightly together that my elbows touched. The rattle of chain was heard as it was attached to my cuffs and pulled upward. The only thing mobile was my head and my legs..but not for long! Cuffs were attached to my ankles and connected to chains which were ratcheted apart. And stopped allowing them from moving anywhere but forward and apart. but not together. With the flick of a switch a bright light lit up my face. In front of me were mirrors in three different angles. i could see the video camera behind me mounted to the ceiling and angled directly in to the mirror at my face! He was going to record my deflowering! i struggled but could hardly move an inch.

"Calm down bitch..you new this was cumming!...." He said as he smacked my ass hard reminding me of my current condition. Strapped down tightly in a pink nightie and heels makeup and what's left of my lipstick still drooling and dripping from my chin with his cum...i no longer felt like person..but a toy...a FUCK TOY!

"I've decided to accept your offer and allow you the opportunity to try and become my bitch..You better work hard though..i have no time for games.So far you've shown some potential to eventually become a decent cock sucker. Now we will see how well you fuck!"

My ass hole twitched as I new it was about to be speared by a hugely erect and hard cock for the first time...I couldn't move an inch!

"Here is your final choice. Either you pussy out and decide to live the rest of your miserable life in shame as you will be known from cost to cost as a cock sucking fag or you have a chance to convince me your worth keeping by begging me to fuck your tight little ass!"

i felt His finger jam into my ass as he lubed me up for his throbbing member! My whole body felt weak and defenseless as there was entirely nothing i could do but start begging him to fuck me like the cheap whore i had become!

He laid his massive tool over the back of my ass and asked me one last time..

"So tell me slut..what is it you want me to do?......"

In final desperation i lowered my head and closed my beautiful painted eyes and pulled against my restraints knowing all to well i had reached the pinnacle of my own debauchery.there would be no turning back after this...i thought long and hard as His cock pulsed laying on my ass ready to make me his new bitch! i raised my head and stared straight into my own eyes through the mirror and uttered the very words that would forever change my life..i took one last breath and then..

"Master..please i beg you to take this whore and make me your own..fuck me long and hard..Master.and teach me to serve you..i offer you this my virgin ass to do with as you please Master..i am yours"

The next thing i remember was closing my eyes and my entire body going stiff as i felt his grip on my hips as his cock slid down and with one hard and long thrust split my anus wide open as i screamed in pain..

Now setting here in the passenger seat of this 747 i can barely move as my ass is still on fire from its brutal assault. Master decided to take my offer of allowing me to finish up and tie up all loose ends back home and finish my career for him to receive all benefits of my retirement. i still had to find a way to dissolve my marriage and make sure my family was taken care of before relocating after my job was over. There was to be no ties and no trace of me in any way shape or form. He told me He would reveal my online training plan as soon as i arrived back home and E-mailed him to let him know I was there. My imagination went wild with what he had in store for me. But enough about my future..i still had to find away to get home unseen from the airport wearing my flip flops, bright pink daisy duke cut off shorts and a pink spaghetti tie tank top which read simply "TAKEN".