A Cockold Sissy Part 1

By Tiffany Scott 2006

enise, the woman I had been married to for the last 11 years knelt
between my spread legs with one hand planted firmly on my lower back
for added support, while she grasped the terrifyingly huge cock that
stuck out where her thighs met with the other. She laughed as she
listened to the muffled sounds that managed to make their way past the
fat ball gag filling my mouth.

“Oh don’t worry my sweet little bitch,” She coo’d as she rubbed the fat
bulbous head of the massive rubber cock over my tight virgin asshole.
“I promise I’ll be gentle like you always promised me every time you
forced me to let you take me there.”

She watched as some of the excess gel she had used to lube my hole
began to coat more and more of the fat rounded head of her cock. She
couldn’t stop herself from laughing at my fruitless attempts to pull
myself free of the wide leather cuffs surrounding each of my wrists.

As she moved further up between my spread legs and her knee’s pressed
against the inside of my legs she felt my thighs harden each time I
attempted to escape from the strong cord tied to each ankle.

“God I get so hot watching you struggle like this!” She exclaimed
gleefully. “It gives me a rush of power and excitement that I’ve never
felt before.” She added as she guided her cock to my gel lubricated

She excitedly informed me that she already knew she was going to be
using me like this quite often in the future as she began pushing her
hips forward hard enough I could easily feel the increase in pressure.

Reading this you may be a little confused about how a manly, semi-macho
type guy like me ended up tied face down on the bed under his wife like
I was. To tell you the truth it was my own fault. You know
Socialologists say that humans are the only animals that will walk
right into a dangerous, destructive situation with their eyes wide open
and I can assure you that they know what they are talking about.

You see one night about a year ago while my wife and I laid in bed
cuddling I had had told her about a fantasy of mine that had grown and
grown until it was just about the only thing I could think about, in or
out of the bedroom. Over the 11 years of our marriage we openly
explored just about any sexual idea each of us had thought might feel
good or thought was exciting.

But neither of us had been so consumed by something the way the idea of
her having sex with some other man had done to me. I had brought the
subject up to her several times, but she didn’t seem to be remotely

As for me? Well, the more I tried to not think about it the more it
grew until that idea had forced every other thought to the back of my
mind. In fact for several months it was all I thought about when we had

That night I had told her about it she could tell that I was serious
and after a bit of questioning she could tell just how deeply effected
I was by the whole idea of it all. Actually I was surprised that she
hadn’t gotten upset or flipped out about it like I thought she would.

In fact as we laid in bed that night and she questioned me she began to
realize how obsessed I had become with it. Of course she wanted to know
what I thought was so erotic and exciting about it and I tried to tell
her, she also wanted to know why I wouldn’t feel threatened by knowing
some other guy was filling her pussy with his fresh cum.

Over the following couple of weeks she learned just how much I had been
thinking about it by making me tell her the things I had been thinking
after a couple of weeks she had gotten me to tell her everything I’d
been fantasizing, even the things I had wanted to keep secret because
they were kind of embarrassing.

You see we had always indulged in long, intense foreplay and once I had
told her about this she would work me up into a frenzy so I was half
crazy with lust. She knew what to do to get me like that and then she
would keep me right on the edge of cumming and would easily tell her
anything she wanted to know.

She was amazed hearing that I fantasized about being forced to help her
get ready to meet some guy by maybe having to pick which pair of her
sexy panties for her to wear and she just sat with her mouth half open
hearing how I would have to listen to her telling me every detail of
what had happened once she had come back home.

The whole scenario had been worked out again and again in my head to
the point that I even described how one evening she would suddenly tell
me that a really good looking guy where she worked had asked her out on
a date and that she had told him yes.

The more she heard and the more she thought about it caused her to
rethink how she looked at me. I didn’t realize it at first, but I
should have realized that when she started to verbally tease me saying
things like no real man would ever want to share his wife.

She would see me blush and tell me my knowing what I was suggesting was
naughty caused me to do that. “And you wanting me to tell you every
detail afterwards is just plain nasty!” She teased playfully.

But I could tell that little by little she was finding the idea erotic
and it also was very obvious that she enjoyed teasing me and
embarrassing me about it.

“Do you want me to suck his cock too?” She would ask lovingly how
questions like that would embarrass me so much my face would turn
bright red and often when she would say things like that to me I would
suddenly erupt and shoot my cum all over my tummy or into her hand of
she was rubbing me.

I didn’t really even think about it but she found it so easy to make me
climax just by saying naughty, sexy things that it we hadn’t actually
fucked for almost three weeks. This just gave her more things that she
could humiliate and tease me about and she would belittle me and
question my manhood every chance she got.

“The only thing that excites you now is thinking about me dating real
men and fucking them!” She would say in a taunting voice. “You would
rather think about that then have sex with me.” She would add. It
wasn’t too long before she was telling me that after thinking it over
she would love to make my fantasy come true.

“It would be exciting to come home with my dates cum in my pussy!” she
said. “And I would make you listen to every little detail of me getting
fucked while you smelled my wet panties that saturated with my and my
dates cum that had leaked out of me!”

There was no way for me to hide how turned on I got when she teased me
or said things like that to me and after she had made me orally get her
off sometimes two or three times she would make me jerk myself off in
front of her.

When she made me to that her teasing was terribly humiliating. She
would call me all kinds of names and say that she couldn’t understand
how she had ever gotten the idea that I was a real man and she would
eagerly scoop up my cum and force it into my mouth and make me swallow

After a couple of months she had me wearing her panties every day,
telling me that only real men wore boxer or jockey shorts. I was
embarrassed that I enjoyed the way her nylon panties felt on my ass and
cock when I wore them and every time the sensation of them rubbing
against me made me hard she would tell me how pathetic I was and say
how she just couldn’t imagine ever letting me fuck her again.

Of course since she loved teasing me and humiliating me so much it
wasn’t to long before she had me wearing her bra’s as well and she was
so discussed that wearing one excited me as well she angrily told me
that anytime I was home I was to be wearing a dress or skirt and blouse
over my panties and bras.

I loved the naughtiness of dressing in her things and I didn’t object
much when she insisted that I start to shave my body hair and wear
nylons and heels as well as all the rest.

Then one afternoon she came home and found me playing with her makeup.
She ranted on and on about how obvious that I wanted to be a girl and
saying if that was what I wanted then I should be as good a girl as I
could be. Once she had said that she made me sit while she cut and
styled my shoulder length hair into a very feminine style and started
making me use her hot rollers every day and she even had me get my ears

Then one day she showed me a shastizmet sheath. “A pathetic sissy like
you has no use for a penis, even a tiny one like you have!” She
exclaimed as she locked it on me.

Several times she invited some of our friends over for drinks without
telling me and then gleefully showed me off to them. I nearly died of
shame when she made me stand in front of one of my long time bowling
buddies and lift my skirt up so he could see the pretty girls panties I
was wearing.

I was forced to do all the household chores and if she was the
slightest bit unhappy with my work she would drag me over her knees and
use her hairbrush on my ass to punish me. Several times she tied me so
I was helpless and couldn’t get away.

Then using one of leather belts she beat me until I had thin red welts
on every part of my body while saying I was just getting my just
rewards for being such a little sissy and not having a real pussy
inside my panties like there should be.

I was stunned one Saturday afternoon after being gone for several hours
she stood right in front of me and said that she hadn’t gone shopping
like she had told me. “What I was actually doing was getting my brains
fucked out!” She said.

My mind went blank and I just stood and stared at her unable to think
of what to say. She laughed and then forced me onto my knees, then
after raising her skirt she rubbed her just fucked pussy into my face.
The wet crotch of her panties had the same smell I recognized from her
feeding me my own cum.

She laughed as she told me who she had been with. “Your ex boss Allen!”
She said knowing that he had fucked my wife would make me feel like
even less of a man then I already did, He had always given me a hard
time and several times at company picnics and such he stood right in
front of me and had asked Denise how come she had settled for someone
like me when she was such a hot looking babe.

“And I am going to continue letting him fuck me!” She told me. “So get
used to it because sooner or later I’m going to let him spend some
nights here.”

She saw the look on my face when she said that. “And your going to make
yourself up all pretty like you love doing so he knows that your no
longer any threat.” She told me. “In fact I wouldn’t be surprised if
you ended up sucking his cock, just so you learn your place.”

She was delighted to watch how I worthless and insignificant hearing
all of this made me feel. “I knew you would get all moody and pout
about it!” She told me “And I think the best cure for you would be for
you to start being with men!”

I objected but she slapped me and told me to shut up. Then she told me
that she had seen things coming to this end and that she was going to
start training me so men could pleasure themselves by using me.

I looked at her with a confused expression as she hooked her thumbs in
the elastic waistband of her panties and stripped them down her legs.
She rolled them into a ball and after stuffing them into my mouth she
almost dragged me into the bedroom.

She forced me onto the bed and then struggled with me until she had
secured the leather cuffs that now held my arms around my wrists. Then
she tired my legs, stretching me out tightly as she could so I wouldn’t
be able to move more then a half inch in any direction.

I watched as she went to her dresser and then removed a strap on dildo
form one of the drawers. Once she had secured in place I saw that it
was so big it’s own weight caused it to point downwards instead of
straight out from her crotch.

She told me that I was so pathetic that the only thing I was good for
was being a slut for whatever man that wanted to fuck me. “Someplace
for them to deposit their cum!” She said and she assured me men would
be fucking me quite often once I was broken in.

“I know Allen would jump ant the chance to bring some of his buddies
here to fuck you while he and I watched!” She said laughing. “He would
be happy to do that just to humiliate you!”

I tried to catch my breath when I felt her toss my skirt up onto my
back. I had to gasp several times in order to draw in air past the cum
soaked panties filling my mouth.

When I felt Denise starting to pull my panties down over m upturned ass
I franticly pulled at my cuffs around my wrists and the cords tied to
my ankles.

Denise sat between my legs and watched my useless struggles. “Your not
going anywhere slut.” She told me. “You should just accept the fact
that tonight I am going to rape your virgin ass!” She added with a

She roughly pushed K-Y lubricant into my ass, forcing it into my hole
with her fingers. Each time she did this her long sharp fingernails
painfully against the sides of my tender hole. I laid there helplessly
as she did this again and again, packing my ass with the slippery goo.

“That should be enough.” Said softly talking more to herself then to
me. “At least I hope it is because my cock will rip you if it isn’t.”
she told me.

When I felt how fat the heed of her cock felt once she was rubbing it
up and down over my lubricated opening I began to roll my head from
side to side while trying to beg her to not do this to me. But all I
managed to do was to make a bunch of recognizable muffled sounds.

Hearing this Denise patted my ass cheek. “Okay. Calm down.” She told
me. “I know your eager to feel my big cock filling your ass, but we
have all night. No need to rush this. I mean it is your first time and
that’s special for every girl!” She told me in a mocking tone.

She was teasing me by continuing to rub her cock up and down between my
ass cheeks. “Oh God.” She said. “I wish you could see just how massive
my cock looks compared to your tiny little sissy hole. This might be a
bit harder on your then I first imagined. But it has to be done!” She
added. “I mean I can’t see any advantage to putting it off.”

I felt her moving, positioning herself so her cock was directly in line
with my hole and then I felt it pushing against my puckered cock
tunnel. The pressure increased more and more until it was pressing
against me hard enough that all I could think about was that when my
opening did give way there was so much pressure that it would stab all
the way into the back of my tummy.

Just as that thought entered my mind my poor opening began to loose
it’s battle to keep the foreign object out. I thought I felt her cock
began to move into my opening. As it did this it was forcing my hole to
stretch open wider and wider around the lube covered head of her cock.

I had never taking anything like this before and wasn’t prepared for
the intense stabbing pain that radiated out from my hole, into my inner
thighs and down through my groin. I started to cry out into my panty
gag in one long wail as Denise gripped my hips harder.

The pain of being stretched open like this was so intense I knew that
my wife’s cock had to be ripping my opening. Then suddenly I felt the
head of her cock slowly move through my opening, disappearing into my
ass. The unbearable pain remained at the same intense level, the only
differencing it began to radiate outwards from deeper inside me.

Several times my ass gripped her cock so tightly that she had to pull
it back a quarter inch or so and then she went right back to stuffing
into me again. She had to be completely ignoring what she was doing to
my sissy hole because she had to be able to see how big it had been
forced to open up.

Tears were streaming down my cheeks and my hack was still stiff and in
the same curving arch it had been when she had started to force her
cock into me.

All I could think was that I was going to die from the pain. But just
then her massive ass ripping cock stopped moving. I felt her lean over
me so her mouth was close to my ear. “I knew you could take all of it
you little slut!” She gasped. “It won’t go any deeper.” She told me,
ramming her hips forward several times as if to prove I had taken as
much as my ass would accommodate.

I was still having a very hard time catching by breath and any movement
he made, no matter how small sent stabbing like pain ribbing out from
what I figured was my ruined hole.

She rested for a bit with her cock impaling me like that, but all to
quickly she whispered into my ear asking me if I was ready. She didn’t
expect to hear an answer and she didn’t wait for one either. As soon as
she had asked that she began to pull her huge murdering cock back out
of me.

This seemed to be just as painful as it was going in and I could
actually feel as if my insides where being pulled out with it. I could
only raise my ass up so far and when I reached that point it began to
slide out of me quicker, but before it pulled out of me it suddenly
changed directions.

This time it sank into me a bit faster then when I was first penetrated
but this didn’t make it any less painful. The only difference this time
was that I actually felt the heed ram into my insides when it bottomed

“Oh God yes!” Denise gasped. “Now I understand why you loved taking me
like this. The feeling of total and complete control.” I felt her dig
her fingernails into my hips to insure she would remain centered behind
her fat cock.

“I’m going to fuck you like this often!” She almost shouted as she
yanked her hips back much faster then any movement before. Of course
she also thrust it back into me faster as well.

The only thought that was strong enough to fill my brain over the all
consuming pain was that I would never live through this.

She was already settling into a slow steady fucking motion and I could
hear her grunt before thrusting her cock into my violated ass each

“Do bet you feel like a girl now don’t you bitch?” She asked as I felt
her raise her upper body off of my back. I could imagine that her
holding herself up like that so she could look down between us so and
watch her cock disappearing into me each time she thrust her hips

Thinking of her doing that caused me to feel more shame and I began
cussing myself out for allowing things to go this far.

“God I never expected that I would enjoy fucking you like this!” She
exclaimed. “I love it.” I could hear her gasping big gulps of air as
she begun fucking me faster. “You take t just like a bitch!” She added.

I suddenly realized that the grunting sound I was hearing was coming
from me. It was the sound of the air being driven out of me each time
she drove the head of her cock against the bottom of what was now my
sissy pussy.

The intense pain I had been subjected to when she had first entered me
had subsided slightly and I realized that I could feel her grinding her
clitty down on the end of the dildo that was strapped against her pussy
each time she thrust into me.

She was making all kinds of sounds. Gasps, whimpers, moans. “I can’t
wait to see you being taken like this my a real man!” She blurted out
between her gulps of air. “Watching you taking them. Hearing you
moaning as they fuck their cocks into you. Using you like the cum slut
that I’ll turn you into!”

In the past I couldn’t stop myself from getting excited when she would
say these kinds of things to me I reacted the same way now. Her words
filled my head with images that I couldn’t control.

“Allen and I will love watching every man we bring here for you fucking
your ass just like I’m doing now.” She gasped. “Standing around you
while each one fills your ass with com, one after the other!”

An image of me on all fours while a strange man pounded his cock into
my sissy ass flashed through my head and then I imagined that three or
four other men would be standing around us rubbing their cocks as they
waited their turn.

Without even thinking about it I began to rotate my hips as far as I
could so that my ass was angled up more in line with her cock each time
she stabbed it into me. It didn’t take her long to notice what I was

“Oh my God!” She exclaimed. “You are a total slut!” She speared her
cock into me with renewed vigor. “Allen bet me that your true slutyness
would be obvious once you had a cock pounding into you!” She shouted.

She buried her cock into me and left it like that as her entire body
was gripped by wave after wave of a mind blowing orgasm. I felt her
legs jerking uncontrollably for the longest time and then she suddenly
gulped down a big breath before dropping on top of me totally

As she laid on me trying to recover she slipped one of her hands under
me far enough that she could wrap several fingers around my sheath
encased chastised cock.

She squirmed so her breasts were pressing against me and made a purring
sound. “You know that this sheath will never be removed. You’ll wear it
for the rest of your life.” She whispered. “Just think of all the men
who be using to satisfy their lust while you will never be allow to cum
ever again.”

I felt her give my imprisoned cock a firm squeeze. “It’s all so
erotically wicked leaving you so that you wont ever get to cum again
and I know that Allen wants that as well.” She told me.

She kissed my ear. “Does that turn you on knowing that your old boss,
who will have the privilege of cumming in my pussy any time he wants,
agreed with me that you should remained chastised forever?” She asked.

“I can’t even imagine what he might decide we should do to you.” She
teased. “He never did respect you and after I told him the things I
have about you he came right out and told me that he wanted to join in
humiliating and abusing you like I do.”

She had a hard time controlling her laughter as he lifted herself up
off of me then roughly yanked her fat cock out of my violated ass with
one hard jerk of her hips. Pulling against the insides of my ass that
had tightened around her cock a bit while we had been lying there
caused searing tendrils of pain to shoot through my sore ass.

“I’ve just got to call him and tell hem that he was right about you
taking it like a total slut once my cock was buried in your hole!” She
said as she got off the bed.

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