Heather s Sissy
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The Sissy Mask free porn video
"Your costume is upstairs on the bed called Penny from the kitchen as I
got in from work. Reluctantly I head upstairs. I did not really want to
go to the Halloween party but know it will only cause a row if I refuse.
I know it will be mostly her girlfriends most of whom do not seem to like
me! I am not sure why because I always treat them with respect. They on
the other hand, seem to treat me with little more than tolerance. Some of
them seem to try to belittle me all the time, my job is not good enough,
I do not appreciate Jenny etc. Despondently I enter the bedroom and my
heart skips a beat. There on the bed is a sissy pink fairy costume, I
move to the bed to examine the dress with its acres of frill. My heart
then falls as I realise the dress is Jenny's, because along side it is a
demons outfit which is probably for me. Both costumes come with half
masks, the kind that are worn at masquerade balls, partially disguising
the wearers face. The demon mast is red and has horns. The fairy mask is
pale pink, the eye holes almond shaped, with painted on thick eye lashes.
I picked up the fairy mask noticing the slight shimmer in the lenses of
the mask. I then have the urge to try it on. So, taking a furtive look
over my shoulder I stepped to the mirror and slipped the mask over my
face snapping the strap into place. Immediately my arms drop to my sides.
All thoughts seem to slip from my head and I stand there watching my own
reflection seemingly mesmerized. Minutes pass and still I am unable to
move. I seem to be paralysed but strangely only in the ability to move.
Even more bizarre is the fact that I am completely calm about the whole
situation. I can hear Penny moving around downstairs and then I hear her
coming upstairs. I should be panicking because here I am with the fairy
mask on gazing at my own reflection. She enters the bedroom and giggles
"I knew you wouldn't be able to resist the temptation." She smiled into
the mirror at me
"You see dear for a long time I have been disappointed with our sex life.
Oh don't get me wrong you're eager and your tongue skills are exquisite.
But you don't have what I need down here!"
With that she squeezes my strangely hardening cock. I want to scream at
her, plead with her but I am unable. My thought are in turmoil but I am
unable to do anything about this.
"The mask you are wearing was rather expensive but it appears it was
worth it. It is called 'The Sissy Mask" it renders the wearer docile and
susceptible to any suggestions. It helps if the wearer is somewhat.......
how can I say......pathetic....submissive. And you my dear fall into both
categories" she sniggers
Again I want to plead my case but I am unable, which reinforces the fact
that she is right on both counts
"Take off your clothes and follow me," she commands.
She takes me to the bathroom and lathers me in a pungent smelling cream.
"We can't have you all hairy for you first debut in public," she quips as
she leaves the bathroom.
I cringe inside realising that my first public appearance will be at the
Hallowen party full of her girlfriends! I know I will be humiliated by
them and strangely my cock stiffens at the prospect. Thoughts of my
coming humiliation are soon lost as the cream begins to burn. I long to
call for Penny but all I can do is stand and wait.
"Oops I'd forgotten about you," she giggled when she returned to the
bathroom.
"Into the shower and rinse off. Then dry yourself and come back to
bedroom."
I implicitly obey her commands, thinking as I do that I should simply
remove the mask. I am however unable to do so.
Dried I return to the bedroom.
"Good girl, now let me have a look at you." She spins me around checking
that all my body hair below my neck has been removed. She then dries my
hair styling it as she does into a very feminine style.
"Now to get you ready for the party."
I quiver inside as I see the first article of feminine attire. It is a
pink satin corset. She wraps it around my body and then begins to tighten
it. I gasp at the severity, but she has no where finished! Soon my waist
is pulled in by a good six inches. I have to pant to breath, much to
Penny's amusement my cock is hard and dripping. She makes me sit on the
bed and proceeds to role a pink gossamer thin stocking up my leg. The
feeling is exquisite against my newly denuded skin, involuntarily I let
out a sigh of joy. Penny smiles a knowing smile. The other stocking
follows and both are attached to the corset. Pink knickers that are
covered with a profusion of delicate frills follow. The petticoats are
next, they are a throth of frills and will make the hem of the fairy
dress sit horizontal! Finally the dress, it is two shades of pink satin
and is awash with frills and bows. I should be balking at this dress, it
is so ultra feminine, but deep down I love it. I would gladly wear it
within the confines of my own home, to wear it in public was going to be
excruciatingly humiliating. My cock throbbed at the thought! Fully
dressed Penny ushered me to the dressing table and began to apply makeup.
As the top of my face was covered she did not need to apply makeup. To
the lower half she applied foundation that matched the colour of the
mask. The match was so good that I could not tell where the mask stopped
and my skin began. To my lips she applied a thick glossy layer of bright
pink lipstick, in the shape of a bow. Looking in the mirror I have an
almost cartoonish face much in keeping with the dress. She leaves me
gazing at my own sissified reflection as she prepares for the party.
Ready she orders me to my feet. I turn and gasp at her costume. It is the
devil costume but it has obviously been tailored for the female form. The
top is cut low at the front displaying her ample cleavage, and the skin
tight suit accentuates her curves. She has painted her own face red to
match the mask
"Now you may speak but you are not allowed questions.....do you like my
costume?" She smiled.
"Yes," was all I could say, I wanted to say more but was unable to.
"You will address women as Mistress and men as Master."
"Yes Mistress" my cock twitched at this new command knowing what it would
entail.
I was lead from the house and into the car, luckily it was dark but then
I mused on Halloween night there would be plenty of costumed people out
and about. We arrived at the party location and my heart sank. It was
Glori's house. Gloria was the one friend of Mistress Penny's who seemed
to despise me the most! When she opened the door to us she laughed
hysterically at my costume. If it had have shown I would have been bright
red with humiliation, my cock however throbbed fit to burst.
"I see you have finally found the wimps true role," she said as she
kissed Mistress Penny on both cheeks
"I told you the mask would be a good purchase."
So it was Gloria who had given Mistress Penny the idea, why should I be
surprise.
"You girl....." she said in a commanding voice.
"You will greet the guests and take their coats, hang them through
there....."
She pointed to a small room.
"You will also hand out candy to the boys and girls trick or treating."
"Yes Mistress Gloria," I answered. Deep inside I simply wanted to leave,
but I was unable, I certainly did not want to be Mistress Gloria's sissy
maid.....although the thought did excite me!
Mistress Gloria and Mistress Penny then waltzed arm in arm into the
party. I was left standing there unable to do anything other than comply
with Mistress Gloria's orders.
Guests started arriving who did not know me, I got curious stares and
sometime disgusted looks, but they did not know me so I felt OK. Kids
started to arrive and on the whole they simply collected their treats
smiling and left. Some of the older kids looked suspiciously at me. And a
couple of teenage girls called me a fag. Then the first of Penny's
friends arrive, Mistress Cynthia. She took one look at me and burst out
laughing. She turned to her husband.
"Jake remember I told you I thought Penny's husband was a complete wimp,
well it looks like I was right, this is him......or should I say her,"
she smirked.
"You're kidding," he exclaimed.
"Yeah I knew he was a small dicked looser but this is special.....show us
you dick sissy," she ordered.
I complied without thought. Well that is a lie, I did not want to debase
myself in front of this woman but I had no choice. Obediently I lifted
the hem of my skirt
"Jeeze....you are tiny.....is it hard?" She smirked.
"Yes Mistress," I answer and my cock much to my shame twitched in
response
"Shit that is small," exclaims her husband.
"Let's go and console Penny, I'm sure she has never had an orgasm whilst
she has been married to this wimp!" Laughs Mistress Cynthia.
They brush past throwing their coats at me and continue into the house
laughing. I have little time to compose myself when a second of Penny's
friends arrive. Mistress Samantha, she is single and an admitted man
eater.
"So it's true then......you are a fag," she states.
"Yes Mistress Samantha."
"Mistress.......I like that, well don't you worry your little sissy head.
I have got someone who will look after Penny like you never had." She
smiles mysteriously and leaves me standing, worrying!
Mores guests arrived and I get the feeling the word has got round because
more and more begin to sneer at me and I hear the occasional "fag"....
Panty waist" name calling. The last of Penny's friends arrived. Mistress
Gemma was a Short dumpy woman with a mean temper. She hated her husband
so she had come on her own to the party. She looked me up and down and
sneered.
"I see Penny needs a real man in her life, perhaps there might be a place
for you to be her maid," she gloated as she hands me her coat.
My mind is awash with questions, but due to Mistress Penny's instructions
I am not allowed to ask them. The question I ask of myself however is why
is this turning me on so much? The guests arriving slowly peters out and
the kids stop calling for sweets, soon I am stood alone listening to the
party getting into full swing inside the house. A few people leave so I
hand them their coats and I realise this is where I will be all night.
Then just as I am thinking this Mistress Gloria appears
"Follow me sissy" she commands tersely. I follow wondering if I am now
going to be used in some other domestic manner. We move through the crowd
until we arrive at the group of friends around Mistress Penny. She looked
tipsy and was hanging onto the waist of a very athletic looking man! When
she saw me a lopsided grin crossed her face and she pulled the man even
closer to her.
"Here SHE!....is......." She smirked at the intimation.
"My tiny dicked....fag.....hubby......Say hello to Max sissy" she
demanded.
"Hello Master," I answered obediently.
"Max is the MAN! Who is going to show me what a real cock looks like, and
use it to fuck me senseless" she sniggered.
I squirmed at her words but was unable to say anything in my defence. The
faces of her friends all pushed in close to see my reaction, they were
all smirking, revelling in my torture. My cock throbbed and dripped at
this humiliation. Then Mistress Gloria spoke, an evil grin on her face.
"Why don't you take Max upstairs and get him ready to fuck your wife,
like you never could...." Her evil grin turned into a snigger.
"Yes Mistress Gloria," was all I could say meekly.
I took his hand and lead him upstairs, as I was going Mistress Gloria
said
"Use the guest room, I made it up especially....it's the second door on
the right....and don't forget to turn down the sheets for the lovers,"
making everyone laugh.
As I led Max upstairs I realised that Mistress Gloria had planned this
all along, the mask, the party and finally Max to pleasure my wife. Of
course my cock was still rock hard! I led Max into the bedroom. There was
a big double bed and little else. I stood by the bed awaiting orders,
then I remembered Mistress Gloria's command so I turn the bed covers down
to allow the lovers easy access to the bed. I then stood and waited
"Well fag!......" he demanded.
"Undress me!"
I complied obediently starting with his t-shirt. The body underneath was
buff and toned. Wash board abs, solid pecks. He must have seen my jaw
drop because he sniggered
"You aint seen anything yet fag!"
I had him sit on the bed, then I removed his shoes and sock. Standing
again, I undid his belt and pulled down his jeans. The bulge in his
boxers looked huge and again he laughed at me. The last item to remove
was his boxers allowing his semi hard cock to spring free. It was huge!
Semi hard it was a good eight inches, and I would have trouble wrapping
my hand around it!
"Stroke it fag...you know you want to......." he sneered.
I gripped the semi soft cock and felt it begin to harden, I did have
trouble wrapping my hand around it. I wondered if it would actually go in
Mistress Penny's pussy. Involuntarily I licked my lips
"Now don't go getting any ideas fag......you're not sucking it....just
get it hard so I can fuck your bitch wife," he gloated.
I continued stroking and soon it had grown to twelve inches, he pulled
away from me and went to lay on the bed casually stroking himself. I
knelt obediently at the end of the bed waiting patiently for Mistress
Penny, my head in a turmoil but my cock hard as rock. Penny arrived
shortly and when she saw Max she gasped.
"Jeeeze....." she exclaimed.
"Stand up Max......and you sissy......Iet me see how they compare! I
gulped knowing exactly what she meant and how humiliating this was going
to be!"
"Lift your skirt sissy," she ordered.
"My god!....no wonder I never got an orgasm," she squealed.
My cock throbbed with humiliation and lengthened slightly, but it was
still a third of the length of Max's monster, they both laughed fit to
burst at my humiliation. When penny had stopped laughing she moved to the
bed and got on head down arse in the air.
"Feed me that monster," she ordered breathlessly.
Max smirked and moved towards the bed. I followed meekly not really
wanting to do it but compelled to do so. I was strangely, starting to
relish the humiliation and knew that if someone were to touch my
straining cock I would burst. Max placed his cock poised ready at the
entrance of my wife's pussy. I could see her wetness glistening on her
pussy lips
"Put it in now!.......I need COCK!" she demanded.
I took hold of Max's cock, it was hot and hard as iron. I directed it at
Mistress Penny's sopping pussy and Max moved forward. I watched
mesmerised as the plumb of a cock head bludgeoned its way into Mistress
Penny's pussy. She gasped and squirmed at the pressure, and just as I
thought it was not going in the head popped inside. Mistress Penny gasped
at the relief of pressure but Max was unrelenting and slowly he buried
the full length of his cock inside her.
"Ahhhhhhhh....now that ...IS!.... a cock," she murmured.
She then turned and looked at me.
"Now that I have a real cock to pleasure me, why don't you go down
stairs, I think Gloria has a job for you." She smiled knowingly.
"Yes Mistress Penny," was all I could say.
I turned catching Max's gloating smirk as I left. I was so confused, I
did not want to see my wife get fucked by that stud, then again I did,
perversely! What I really wanted was to watch her pleasuring herself, as
it was I was not allowed to. To add insult to injury I had only got half
way down the stairs when I heard her screaming out her first orgasm,
probably the first of many I thought. I found Mistress Gloria in the
Kitchen, she gloated at me
"Is your wife getting fucked by a real man?" She smirked.
"Yes Mistress Gloria," I replied meekly my cock twitching angrily.
"Follow me sissy, I have a task for you."
I followed her through the kitchen into what appeared to be a utility
room. It was long and narrow with the washing machine and tumble dryer
down one side. Also in the room were Mistress Cynthia, Mistress Samantha
and Mistress Gemma, they all smirked when they saw me. In the centre of
the room was a wooden stool facing the workbench at the end of the room.
On the bench was a laptop displaying two pictures. One was showing a
webcam view of the room focused on the stool. The other I was unsure of.
"Over the stool," ordered Gloria.
My knickers were removed and I was bent over the stool. I felt so
vulnerable, especially since my bottom was exposed to the whims of my
sadistic captors. Once I was over the stool I was tied hands and feet to
the legs of the stool by Mistress Samantha. Someone took hold of my hard
cock and forced it under the seat of the stool.
"Head up sissy.......and keep it up," came the order from Mistress
Gloria.
I looked up into my own face on the computer screen. I could also see
that the other camera was under the stool pointing directly at my cock.
It was forced under the seat at a forty-five degree angle, it was also
pointing directly into a pint glass! Mistress Gloria appeared in front of
me and spoke to Mistress Cynthia who had moved in front of the laptop.
"How many viewers?" she queried.
I worried as to what she meant by viewers.
"Just over one hundred.....but more will join when word gets around." She
smiled knowingly at me.
"OK, let's get the show started," said Mistress Gloria.
Mistress Cynthia moved aside, and Mistress Gloria turned to the laptop.
"Ladies and Gentlemen, place your bets, see how long it takes to make
this virgin sissy squirt her sissy juices.......the rules.....each
Mistress has fifteen minutes.....she can use whatever weapon she
chooses...time starts when she enters the sissies pussy."
I was shocked when I realised what was going to happen. I was going to be
the entertainment to a group of online voyeurs, not only that Mistress
Gloria was going to make money out of humiliating and debasing me. My
cock throbbed with excitement!
"First to test the sissy is Mistress Cynthia!"
At that Mistress Cynthia stepped in front of me. When I saw that she had
an eight inch dildo strapped between her legs I gasped in shock, my eyes
wide
"That's right sissy......this baby is going to make you shoot your sissy
juices." She smirked.
She moved behind me and I felt a cold blob of lubrication hit the crack
of my bottom, this was unceremoniously massaged in with two fingers,
then.....
"Ready.....go"
On go the strap on plunged into my pussy. It was not brutal, she simply
plunged the whole length in, in one go. She then began to slowly fuck me.
"Come on faggot...sissy....fuck slut......shoot sissy....."
I realised as I stared into my own now lust glazed eyes that the mikes
were open and the audience was able to shout insults at me. I was totally
hyped up and ready to come before the start of this new humiliation so it
was no surprise that I came in one and a half minutes. I watched my cock
shoot into the glass as ribald comments rang in my ear.
"One minute thirty seconds......." sneered Mistress Gloria.
"No wonder Penny was looking for a real man!"
My wilting cock twitched at the comment. I was allowed a moment's pause
as they took in their winnings and paid out to the winners.
"Next round is my turn," said Mistress Gloria.
When she moved into view I gasped again. The strap on she was wearing was
around twelve inches long and thick! She lifted my chin even further to
look into my eyes.
"You may recognise this monster..." She smirked.
I was at a lost to understand her, smiling a knowing smile she continued
"This is a replica of Max's cock. I made an impression of it last week
knowing he would be fucking your wife with it. Just think while your wife
is upstairs getting fucked by the real thing, you are downstairs getting
fucked by the replica," she gloated.
My wilted cock was now hard and throbbing at this new humiliation.
Mistress Gloria disappeared behind me.
"Ready....Go!"
I felt the plumb of a head push against my pussy. The pain was intense as
it forced its way in and then as the head popped inside she plunged it
all the way in.
"That's it bitch take it all just like your wife did," sneered Mistress
Gloria.
The vision of Max's cock sliding into Mistress Penny's pussy filled my
thoughts, and due to this I was shooting my juices in no time at
all......again!
"Fifty-nine seconds............what a looser!" laughed Mistress
Samantha.
"Fuck....she is pathetic.....boooo......fag....cock slut," came from the
audience.
Again winnings were taken and then it was Mistress Samantha's turn. She
used a ten inch strap on and the fuck was savage and brutal, I managed a
better performance at nine minutes fifty seconds this time however and my
climax was a dribble. The final Mistress was Mistress Gemma. Her strap on
was rather strange. It was a lot smaller and had a downward kink.
"Ready....Go!"
She rubbed the strap on across my prostrate twice and I started to leak.
There was no orgasm and at first I thought I was peeing. When I looked at
the screen I realised it was my spunk!
"Shit....I didn't have enough time to start the clock," laughed Mistress
Gloria.
"You bitch Gemma your milking her!...........well since you got her to
shoot the quickest why not fuck her for the full fifteen."
This is exactly what Mistress Gemma did and I leaked continuously. By the
end my balls were aching and I was down to a dribble, but the glass was
half full with my spunk! Finally to my relief the milking stopped, but my
ordeal had not ended yet. Mistress Gloria stepped in front of the laptop
swilling the contents of the glass.
"Final wager of the night folks......how long will it take sissy fag to
drink her own juices?" She smirked at me over her shoulder. My spent cock
unbelievable began to stiffen much to the amusement of my Mistresses and
the audience.
"Not only is she a cock hungry sissy, she appears to be a cum dumpster as
well" laughed Mistress Gloria.
At this humiliation my cock stiffened to hardness again. Mistress Gloria
handed me the glass and I looked at it worried.
"OK, folks place your bets."
This gave me time to contemplate this latest humiliation and
unconsciously I licked my lips, this unfortunately was picked up by
Mistress Samantha.
"It appears the fag is desperate to taste some spunk," she smirked.
"OK sissy....ready....go!"
I thought I would simply gulp the contents of the glass straight down but
that was easier said than done. The taste was strong, salty, metallic and
sticky. Pretty quickly my mouth clogged up and I had only drunk half of
the contents of the glass! I lowered the glass and gulped in air.
"Hurry up cum slut," admonished Mistress Gloria, with that she pushed the
glass into my face. This had the effect of sloshing the spunk over my
lips and down my chin.
"You spilt some bitch!" came from the audience.
I drank the final half in two sessions hoping my ordeal was now finished.
But Mistress Gloria had other ideas
"Scoop the spunk off your chin cum slut, and then lick the drops that
went on the floor!" she ordered.
At the last drop licked from the floor.
"Stop the clock........fine minutes twenty seconds......Hell she is a cum
hungry slut!"
Once the bets were finished I was left sitting on the floor facing my own
cum sticky face. Gradually the audience or five hundred and eight! Began
to signed off until there was only one person left. Someone called 'Black
Stud'
"Stand up sissy and show me your pussy," came the order through the
laptop.
I obediently complied, I heard him chuckle.
"I sure would love to fuck that sissy pussy," he mused.
I thought to myself that I was glad he did not know who I was or where I
lived. This comfortable thought was shattered by his next words.
"I thought I recognised the mask sissy....."
I quickly realised he knew what power he had over me.
"What's your name and where do you live?" he asked.
I of course obediently gave him everything he needed, knowing I would
soon be his bitch!
"Well sissy I got to now......but I will be seeing you soon" with that he
logged off.
Sometime later Mistress Gloria appeared, she threw down the keys to my
car and spoke.
"Go home cum slut! Penny has decided to stay the night and experience
Max's morning wood," she smirked.
"When you get home you will undress, the last thing you will take off
will be the mask."
I drove home and as ordered undressed. I sat at the dressing table and
removed the smeared leftover makeup. I then reached up and removed the
mask. Immediately I came out of the stupor that had, had me at the mercy
of others all night. I knew I should have thrown the mask on the floor
and smashed it to pieces, but I did not. Instead I placed it reverently
on the dressing table! I got into bed and stroked my hard cock, my climax
was feeble and I then fell into an exhausted sleep.....
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