Sissy New Year
- 4 years ago
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Sissy New Year free porn video
Author's note: My stories generally featured a lot of forced femme,
bondage and kinky sex--you know, the stuff that I keep hoping will someday
happen to me.
That is still true for this story, but this time around, the author in me
decided to spend a bit more time developing the characters before
commencing the full-on sissy sex orgy. I also wanted to write a story
where the characters are well intentioned instead of simply being a
rogue's gallery of perverted bastards. With that in mind, I hope that you
will still enjoy this story, even though it takes a while to get to the
good stuff.
As always, I welcome your comments, and happy sissy new year to all.
xoxo
Sissy Michelle, aka Emshoninque
1-Sissy New Years Eve
My boss, Robert Stinson came into the sales bunker mid-morning on December
31st. "Guys," he said, "and girls," he added as he motioned toward Brenda
and the two sales assistants in the room, "I've got some great news."
We all gathered around as my boss announced our final December numbers.
"That's twelve months straight," he said with a big smile on his face.
"It's one thing to make budget, but to have the entire team hit at least
112% for the entire year hasn't ever been done before."
He went around the room and shook each one of our hands and announced that
not only were we going to close the office early so that we could start
our New Year celebrations, but that he wanted to take us all out to lunch
first. If that wasn't enough reason to cheer, he handed out our bonus
checks and said that he didn't expect to see anybody back in the office
until next Wednesday.
The room erupted in happiness at the prospect of a 5-? day, fully paid
holiday weekend. I chimed in with a half-hearted smile, but truth be told,
I wasn't really looking forward to having so much time off from work.
I suppose that I should explain. I am a 38-year old single man without any
family here in town. It's tough getting through the holidays when you're
all alone. Most of my friends are here at work, and I knew that they would
all be off celebrating with their families. I was going to spend my free
time alone in my apartment, probably going through a case or two of wine.
I was also horny as hell and had absolutely no prospects for relief.
My boss noticed that I didn't seem as thrilled as the rest of the group.
"Let's get out of here," he said as he put his arm around me. "I think
Mike needs a drink, and I'm buying."
There were more cheers as we all gathered our coats and locked the office
up for the weekend. Within an hour we had all reassembled at a very nice
steakhouse here in town. Everybody was treated to steaks or lobster. The
wine flowed with no regard to price and nobody skipped desert, although
our two assistants, Janine and Caroline both mentioned that they wouldn't
be able to fit into their party dresses if they ate anything else.
I saw several of the guys at the table smile. Janine and Caroline are both
fresh out of college and complete knockouts. I could tell that many of the
guys were imagining what they would look like in their party dresses. If
their office attire offered any clues, some lucky partygoers were going to
be treated to the sight of two very sexy goddesses on the prowl tonight.
I noticed Brenda smiling as well, and for a fleeting moment I wondered if
she was fantasizing about the assistants as well. But then I thought that
she was probably thinking about her own party dress. Brenda is in her
forties, but certainly doesn't look it. She is drop-dead gorgeous and
oozes confidence. I'm not alone in thinking it to be very sexy. Not to be
catty, but I know that there are some clients that stay with us because
they love having somebody as beautiful as Brenda serving their account.
I must admit that I have fantasized about Brenda in the past. Well, not
about Brenda, as much as about being Brenda. Here comes the real
explanation behind this story: You see, my deepest secret is that I am a
closeted and very frustrated crossdresser and would have given anything to
be half as beautiful as Brenda.
I spend my days dreaming about what it would be like to be sissy Michelle
all the time. I spend my weekends trying to make this come true.
I love coming home from work on a Friday evening and running a hot bubble
bath. I proceed to shave my entire body and then begin the process of
dolling myself up. I have some scented lotion that is the same brand that
Brenda keeps in her desk drawer. It smells divine. I rub the lotion into
my skin, paint my nails, put on my lingerie and do my makeup. Breast forms
are glued on and my corset is cinched as tightly as I can get it. Hose,
hair and heels complete the look. I'm not going to win major beauty
pageants anytime soon, but I'm generally happy with the results.
It usually takes about three hours to get all dolled up and ready to spend
the weekend as sissy Michelle. I used to jerk off while dressed all
weekend long, but I found that I loved staying horny and on edge for long
periods of time, so a little more than a year ago I purchased a Jailbird
chastity device and found a online keyholder who claimed that he would
turn me into the sissy slut of my darkest fantasies.
That was a lie.
Not to be ungrateful, but serving Master David, as I had been instructed
to call him, proved to be a disappointment. I was looking for somebody who
would give me a push and help turn me into the sissy I wanted to become. I
was looking for somebody who would put me on my knees and bring me lots of
cocks to suck. Master David only wanted an online sissy that he could jerk
of to while he watched from afar.
To be fair, thing started off well. Master kept the key to my chastity for
three-month stretches at a time and would only send it back to me if I had
been a "good gurl." Being good meant acting like a bad girl in front of my
webcam for Master's pleasure--I certainly enjoyed that.
I had been instructed to purchase a full-length mirror and a dildo with a
suction cup base. I'd spent many evenings on my knees servicing that
rubber cock while Master David watched me from the other side of the
country. I kept wishing that one day it would squirt in appreciation of a
good job.
Alas, Master had said that he didn't share his sluts, so I had been
forbidden to seek out any local men to play with. This certainly kept me
horny and frustrated. I had to content myself with servicing my dildo and
dreaming about something more.
I kept telling myself that one of these days I would get a flesh and blood
cock to service, perhaps even one that was attached to someone I could
actually call my boyfriend. That was just a fantasy. I hadn't done
anything to make that dream come true over the past year as Master David's
sissy pet.
You're probably wondering why I didn't just leave Master David. I know
that I could have cut the lock to my chastity with a hacksaw, but Master
David had been taking pictures of me sucking on a dildo as sissy Michelle
for a while and he threatened to expose me if I ever disobeyed his orders.
As proof of my submission, he'd instructed me to begin each sissy training
session with an incriminating mantra.
"My name is sissy slut Michelle," I would say while looking directly into
the camera. I would then reveal my full given name, home address, cell
phone and email address. I would then proceed to chant, "I am a sissy
slut. I am nothing but a cum dump whore who lives only to suck cock and be
fucked like a good slut. Please come claim me and train me. Take me and
make me into your sissy slut. Thank you, Master, for turning me into your
obedient little sissy slut."
I would then proceed to spend the next thirty minutes sucking on the
dildo. I would then turn back to the camera and repeat my sissy mantra. I
never knew if Master was watching me or not, or if he was recording my
performance on his end.
I realize that I only had myself to blame for my predicament. I had no
excuse other to say that I was horny (and a little bit drunk) when I
initially signed up, and then I was scared shitless of being exposed.
Master had threatened to post the video and pictures online and send a
copy to my work. I would certainly lose my job, and then he'd find
somebody to come over and turn me into a sissy whore in real life, whether
I truly wanted it or not.
Master was deadly serious, so I kept playing along, going through the
motions of being his online sissy while I dreamed of better things to
come.
I never dreamed that a better sissy life would be coming my way on January
1st. I didn't actually make a resolution to become a full-fledged sissy
slut in the new year, but that's what happened anyway.
Back to the story.
After our celebratory lunch broke up, I hit the liquor store and then
headed home to get dolled up for a very long weekend. By 7pm I was ready
and waiting in front of my camera, but Master didn't come online. I waited
like a good sissy. Nothing happened. I put the dildo on my chair and
bounced up and down while I waited for Master.
I started drinking.
And drinking.
And drinking.
I was pretty blitzed by 9pm when I finally gave up. I was also horny as
hell as I'd been fucking myself sissy these last few hours, and I'd been
locked in my chastity device for the past six months without any release.
I couldn't stave off my desires any longer, so I logged onto Craigslist
and finally posted the ad that would transform my life.
The title read: "Come Make Me Your Sissy for the New Year." Which was
followed by "Sissy in chastity needs a horny man to come use her like a
complete slut. Extra points if you can stop by every day this weekend, or
every day from here on out."
I attached four of my favorite pictures of me on my knees sucking my
practice dildo and then posted the ad.
I swear that it took hours for the ad to finally appear online, and
because it was New Years Eve, I didn't get many responses at first. I kept
drinking and riding my dildo and wishing it was the real thing. By 11pm I
was so horny that I vowed to do anything in order to suck my first real
cock that night.
Tyrone send me a message just after 11pm. He told me that he was going to
a party, but wanted a sissy slut like me to be waiting to swallow his
first load of the New Year.
I immediately wrote back and agreed.
He asked if I had ever been a bondage sissy. My sissy clitty was rock hard
in its cage as I replied that it had always been my fantasy.
By 11:30, as per Tyrone's instructions, I had unlocked my front door and
put a small piece of pink duct tape on the doorknob. I'd used the rest of
the roll to bind my ankles and knees together. More duct tape served as a
blindfold. I used the last little bit to awkwardly bind my wrists
together, using my mouth to tear off the last bit of tape.
And then I waited while my clitty kept throbbing in its cage. I heard the
fireworks signal midnight, and I stayed tied up on my living room floor,
hoping that tonight would signal the beginning of my new life.
Eventually I fell fast asleep, but woke up immediately when I heard my
front door open in the middle of the night and footsteps and hushed voices
told me that two men had come into my apartment.
"See, I told you," the first mystery man said. "This one's a horny slut."
He chuckled as the second man felt my ass and agreed, saying, "I'm gonna
enjoy spit-roasting this bitch."
I heard the sound of a switchblade knife opening and the duct ape was cut
loose. The two men lifted me to my knees. They dropped their pants and
before I could say a word a cock was shoved roughly down my throat. It was
big, but not as big as my dildo, so I didn't really have any trouble
swallowing it to the hilt.
I was caught up in the enjoyment of my first real cock when the second man
flipped my skirt up and started sneaking his hands inside my panties. I
was still well-lubricated and stretched out from earlier. "Damn," the
second man said. "This bitch is greased up and ready to go."
Within moments I had a cock in my mouth and another one in my ass. They
held still while I rocked back and forth. It was a wonderful feeling, and
I wondered why I'd waited so long to serve as a sissy for real men like
these.
After a while my they decided to switch places. I'm glad that I had
cleaned myself out earlier in the evening, and Tyrone loved that I didn't
balk at the thought of sucking the cock that had just come out of my ass.
I was still blindfolded, so I couldn't tell what Tyrone and his friend
looked like. In my mind's eye I imagined a very hot scene where two men
skewered a sissy, so I pulled off of Tyrone's cock just long enough to ask
him to take a picture for my "sissy scrapbook."
Tyrone laughed. "Sure thing, baby," he said. I think we can start a whole
photo album for you." He asked for my cell phone and I told him that it
was in the bedroom. "Stay here with Daveed," he said as he went to
retrieve my phone.
"Sissy likes posing for pictures, hmm?" Daveed whispered in my ear as he
picked up the pace and started assaulting my ass at full speed. "We're
gonna take lots and lots of pictures for you," he said as he fucked me so
hard that knees buckled and I fell to the floor.
He cock popped out he immediately started spanking my ass. "My cock stays
in your faggot ass until I decide to take it out," he said as he spanked
me mercilessly. "Yes, sir," I said as Daveed positioned himself for re-
entry.
But Tyrone stopped him. "Hey," he said, "bring the slut in here. Daveed
laughed and drove his cock full into me and then lifted and carried me
into my bedroom, his cock still impaled in my ass.
Tyrone was standing over by my computer. My web browser was open to my
email account and my web cam was still on and broadcasting. "So, this slut
put an ad online," he said, "and it looks like there's gotta be 40 guys
here who want to take her up on her offer."
"This one's a real whore," Daveed agreed. "I wish we'd met her before
tonight."
"No worries," Tyrone replied. "We'll make up for lost time. But there's
more. This slut's camera is one and there's somebody named Master Dave
watching us."
Daveed tensed for a moment and Tyrone laughed. "Don't worry," he said. The
camera's pointed down. He can't see anything but this slut gagging on our
cocks. Let's give him a show"
"I'm gonna love using this slut," Daveed said as he put me down and
started fucking me again. "Me too," Tyrone said as he shoved his cock back
into my mouth. This time I didn't move as the two men pounded into me from
both ends.
Some where in there I heard the sound of a web chat window opening up.
Daveed broke away and then asked, "Who the fuck is this Master Dave?" In
between mouthfuls of Tyrone's cock, I told him that "He's my Master. He
has the key to my chastity."
"Well, he's pissed," Daveed said and started reading. "I'm throwing your
key away and sending the pictures to your work. Enjoy your new life as a
sissy whore!"
Both men laughed. "Damn, bitch. You pissed him off." I started to
instinctively apologize, but Tyrone kept my mouth full of his cock so I
couldn't really say anything. Instead, I just moaned like a sissy whore in
heat while both men resumed their assault on my orifices.
Daveed noticed that while Master Dave was angry, he was still watching the
web feed. "I think he's recording this shit," he said. "Fuck that
asshole," Tyrone said as he reached over and stopped the broadcast.
"You're my bitch now."
The time for talking was over. Tyrone and Daveed began pounding into me in
earnest. In my fantasy, they would have both cum inside of me at the same
time, but Daveed pulled out and shot across my ass first. Tyrone covered
my face with his load a few moments later.
"Almost forgot," Tyron said as he took my phone and took pictures of my
cum-covered face and ass next to his cock. Then he put their names into my
contact list under MASTER Tyrone and MASTER Daveed with the pictures as
the profile photos. "Now, when we call you, you'll always be reminded of
the day we first met," he said.
Daveed laughed and added, "That's some romantic shit right there."
Tyrone gently peeled the duct tape off of my eyes. I looked up into the
smiling face of one of the most handsome men I'd ever seen in my life.
Tyrone was tall and covered in muscles. His medium-black skin glowed with
sweat and stood in relief to the giant smile that immediately melted my
sissy heart.
Tyrone was tender to me as he used a warm washcloth to wipe the cum from
my face and ass. He helped me to the couch and then lifted my skirt to get
a better look at my chastity device. Daveed joined in the examination.
"That's some serious steel," he said as he felt the device's weight. "How
long have you been locked up, sissy?"
"Six months," I replied.
Both men said "Fuuuuck" in unison.
Finally, Tyrone said, "Don't worry, baby, I can cut that padlock off
anytime you want." After a moment's hesitation he added, "And I could put
one of my locks on, if that's what gets you off."
My clitty immediately jumped at the idea and both men laughed.
Tyrone sat and pulled me to his lap. "Okay, baby," he said "we're gonna
have some fun. Tell daddy what you're looking for."
It was if a dam burst inside of me. I sat on Tyrone's lap and confessed
all of my darkest desires. "I want to be a sissy," told him. "One day I
want to be a full woman, with big tits and a pussy and everything. I want
to live my days as Michelle, and I want to spend my nights as a sexy
bondage slut who will do anything to please her Master."
Sitting on Tyrone's lap, I felt his cock come back to life."
"Mmmm, baby," he said, "You're making daddy hard. Go on."
I wiggled my ass as I continued. "I want to come home and find my house
full of Daddy's friends, all waiting to fill my cum holes." Tyrone moaned
and shifted in his seat. I want to spend my nights down on my knees
servicing a never-ending parade of hard cocks. I want to spend my days
eating nothing but cum and washing it down every night with Daddy's piss."
That was all it took. Tyrone's cock was rock hard again. He effortlessly
lifted me up and impaled me down on his cock. I bounced up and down and he
kissed my neck as I went on.
"I want to be tied up and fucked while I'm locked in bondage," I continued
in between grunts of delight.
"I want to be ridden hard and put away wet."
"I want to be fucked and filled full of cum and covered in piss and then
tied up and left until Daddy and his friends come back for round two."
"I want to spend days and days and days tied up and slurping down nothing
but cock, all of it being broadcast to some sissy website where we ask for
donations to help pay for my sissy surgeries."
Tyrone was moaning like crazy now. "You're making me cum," he said and
started to lift me off of his cock. I wanted to stay impaled on his shaft
so I wiggled my way back down his cock. I looked up and whispered into his
ear, "Please breed me, Daddy."
He did. Even though it was his second orgasm of the night, it felt like he
filled my sissy ass to overflowing. What's more, my little cock started to
pulse in its cage without having been touched. The chastity kept me from
getting fully erect, but six months worth of cum was finally let loose.
I was so lost in my sexual haze that I didn't realize that Daveed was
standing there videotaping the whole thing on my cell phone. He had been
stroking his cock while he watched Tyrone fuck me. He didn't say a word as
he stepped forward and shoved his cock in my mouth and immediately flooded
it full of cum.
I remember thinking that this is what a sissy should taste in her mouth
every day.
After a few moments we finally came back to our senses. Tyrone broke the
ice by saying that we were going to have lots of fun. "What are you doing
tomorrow?" he asked.
"Sucking your cock," I replied without missing a beat.
"Damn right," he said as he stood and started dressing. "Maybe tomorrow we
can do some of that bondage shit you were talking about." "Yes, daddy," I
replied.
After a moment, I summoned up my courage and asked. "Could we do some
now?"
"It's late," Tyrone said, "I know you sissies dream about big Black cock,
but you fucked me dry, girl. I'll come back tomorrow morning, but I need
to sleep first."
"No," I ventured in a timid voice. "I mean, could you tie me up and leave
me that way until you come back tomorrow."
There was a pause as Tyrone considered it. "That doesn't sound safe," he
said and I agreed. There was another pause. "But you still want me to tie
you up, don't you?" I agreed once again.
I loved that he came to a quick decision. "Okay," he said. "I've got some
rope in the truck. Why don't you go take a piss or something and get
ready. I'll be right back."
That was smart as my bladder was definitely full. My ass was also
stretched wide, but when I felt Tyrone's cum start to leak out, I hobbled
to my bedroom and retrieved a butt plug that I had in my drawer. It popped
into place without any resistance.
I pulled off the duct tape that was still stuck to my legs and ankles--it
totally ripped my stockings so I threw the whole mess into the garbage. I
quickly changed into a fresh pair of panties and a matching red satin baby
doll nightgown. I was about to wash my makeup off, but I stopped when I
saw my reflection in the mirror. I looked just like a well-fucked whore
and I decided to stay that way, at least for tonight.
I heard Tyrone as he stepped into the bathroom carrying some rope that he
had in this truck. "You sure about this?" he asked. "Yes, Daddy," I said.
I want to be your little bondage sissy slut." There was another moment of
hesitation before Daveed chimed in. "Well, be a gentleman and give the
sissy what she wants."
Tyrone reached in and grabbed a hold of my cage. It was still a sticky
mess, but Tyrone didn't care. He was only checking to see if I was
serious. My throbbing clitty told him that I genuinely wanted this. He
brought his hand to my mouth and I licked it clean.
I was taken back into the living room. Tyrone and Daveed tied my ankles
tightly together. They tied up my knees. They started to do my wrists in
front of me, but I stopped them when I realized that I could use my mouth
to get free. Eager to please, they tied my arms behind my back, and for
good measure they did my elbows as well. Then, without prompting, they
attached my wrists to my ankles and secured everything with a tight knot.
Tyrone covered me with a blanket and then checked one last time to see
that I was okay. I was helpless and I loved every second of it. I nodded
yes and Tyrone smiled. "I won't be able to get back here until later on in
the morning," he told me, "but I'm gonna spend all night dreaming about
that hot sissy ass. Then I'm gonna come over and fuck you so hard that
you'll have a real pussy from now on.
I nodded and said "Thank you, Daddy."
"Good night, sissy," he said as he walked out the door.
Daveed added, "Fuck you later, slut," as they left.
I heard the truck start and drive away and I lay there in the dark
thinking about what had just happened. I smiled to myself as I thought
that maybe this super-long weekend wouldn't be so bad after all.
I wiggled to test the ropes and was happy to see that I was indeed tied up
tight. It felt like I was finally where I needed to be--tied up on the
floor and full of cum and feeling very satisfied. "Happy New Year," I said
to myself as I drifted off to sleep, dreaming of having my ass fucked into
becoming a pussy while I gobbled down a never-ending parade of hard cocks.
I was exhausted from my first night as a real sissy, so I slept soundly,
waking only briefly when I heard Tyrone's voice a few hours later as he
whispered in my ear. "You okay, sissy?" he asked. I practically purred as
I realized that he had come back to check on me. "Yes, Daddy," I said,
smiling. "Thank you for checking on me."
"Okay sissy, get some sleep. We've got a lot of fucking to do tomorrow."
I purred again in anticipation and then went back to my sissy dreams that
were filled full of Tyrone's smile and his hard cock.
I woke the next morning to the sound of my front door being opened and I
squinted as sunlight streamed into my eyes as the blanket was pulled off
my head. I smiled in anticipation of seeing Daddy's cock first thing in
the morning.
Except that it wasn't Tyrone.
Robert Stinson stood there with his jaw hanging open.
"Are you okay, Mike?" he stammered.
I was unable to answer him.
"I was worried about you after you left the restaurant, and then I got
this fucked up email last night while I was in bed. I thought I'd better
come check to make sure you were okay."
I still couldn't say anything.
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