Her Sissy

sissy transvestite with black lips

At the time I had no idea what my wife had planned. We had
been married for three years and I thought we were both
happy, but Kelly was getting itchy and restless. It wasn’t
that she was tired of me or the life we had created for
ourselves, it was more than she wanted to be in control.
That she knew what she wanted almost made it worse because
she didn’t know how to go about getting it. Oh, sure there
were times when she felt the way she wanted to feel. She
felt that kind of power and control when she would tease me
so that I was almost ready to come, then she would make me
beg her to let me fuck her.

She had been thinking about those times when she had taken
the dominant role and after a bit of thinking she started to
realize just how easy it was for her to get me to submit to
her.

Kelly was a bright girl and she gave the whole thing quite
a bit of mulling over. In fact, she had even conducted a
couple of experiments over the last two weeks. Once she
refused to let me come until I had tounged her to numerous
climaxes. Another time she had pretended to be upset with me
and after telling me over and over how bad I had been she got
me to agree to let her spank me.

She couldn’t think of a better demonstration of my
submissiveness then to be bending over while I held my dress
or skirt up around my hips so that she could spank my now
defenseless ass cheeks, unless it was what she was planning
on doing to me.

She hoped that forcing me to listen as she told me how much
she enjoyed punishing me would make me eager to let her do it
to me any time she wanted. “Yes, I think that out of all of
the things we have done together, I enjoyed spanking you like
a naughty little girl more than anything else!” She told me.

She smirked when I told her that I was glad that she
enjoyed it. “Any time I can be part of something that you
enjoyed doing I feel like I’ve done something nice for you.”
I told her, then I added, “If there’s anything else that you
think you would enjoy doing don’t hesitate to try it. Just go
ahead and tell me what you want me to do.”

“Really?” she asked, sounding as if she didn’t believe me.
“You just go ahead and tell me what you want me to do and
I’ll do it.” I told her. She smiled and then told me that she
wanted me to be her slave so that I HAD to do what she told
me to do.

“Then consider me your slave,” I told her. “And I’ll just
assume that I have to comply with anything you want of me.”
She looked at me for a moment, then she ordered me to spread
my legs so that my balls were completely accessible for her.
I swallowed hard and then slowly moved my legs apart until
they formed a wide Vee.

She nodded as she slid her hand up between my upper thighs.
“I love to think that they are hanging like they are and just
waiting for me to decide what I want to do to them.” She told
me.

“They are,” I said. “You own my balls as well as everything
else if I’m your slave,” I told her.
“That’s right.” She said with a smile. “And that would mean
that I had a perfect right to do anything I wanted to them.
Anything at all!” She closed her fingers around the two small
nuggets. “What I want to do to my balls is make them hurt!”
She said wickedly. She then crushed them against each other
as she made her fingers form into a fist.
I doubled up and groaned as my tummy was gripped by strong
cramps. “Oh yes. I can tell that they hurt.” She gasped as
she squeezed them even tighter. My hands pressed into my
tummy as I fought to catch my breath.
“Spread your legs wider slave, as wide as you can!” She
ordered. I heard her laugh when I opened my legs as wide as
they could go. “Yes, now I can do anything I want to them.”
She said. “Even smash them under one of my knee’s!” She added
as she slid one leg up between mine.
She released her grip, then raised up slightly. When she
lowered herself down I felt her hard knee start to flatten
them under it. Once again I was doubled up from the way she
was abusing my balls.

“God, they feel as if they just flattened right out like
squashed pancakes.” She squealed, then she lifted off of them.
“If your my slave and I own your body, then I also own your
asshole!” She exclaimed with a chuckle.
But all and all she still wasn’t sure how to go about doing
what she thought she wanted to do. That is until my birthday
started to get close. She had purchased a new monitor for my
computer and she decided to hide it in the garage.
There were a number of boxes of old paperwork and such and
she felt that one more box wouldn’t be noticed. The Friday
before my birthday she got home several hours before me and
she went out with the idea of moving things around so that
she could stash her present in an inconspicuous spot.
Most of the things were covered with dust and such and she
quickly got fed up with trying to make it look like nothing
had been disturbed. Finally, she had had it and shoved several
boxes to one side so there would be room for hers, but when
they landed on the garage floor she was surprised by what
spilled out.

From her perch on the ladder, she could clearly see all
kinds of women’s clothing. After closer inspection, she knew
that these things weren’t just a bunch of old discarded
garments. Some of the blouses and other pieces were up to
date styles. In fact, she found a slip that she knew was part
of Vanity Fairs newest line.
With a growing curiousity, she looked through the two boxes
of lingerie, dresses, skirts, and blouses. She even found a
fair number of almost new high-heels in the second box along
with a very complete collection of make-up.
She was still a little confused when she picked up the
small square booklet, but her confusion didn’t stay with her
very long as she glanced at the photographs that were inside.
I had been crossdressing since the age of 12 or so and
although I had tried to stop, I found that I couldn’t. I had
never told her about it and dressed up only when she was
away. Over the years there had been some pictures friends had
taken of me when I was completely dressed and made-up.
She was not only surprised to learn about this part of me,
but she was also surprised to see that I made a very good
looking woman. As she glanced at the photo’s a smile began to
appear on her face, a smile that kept growing bigger and
bigger.

After putting the boxes back like they were she put the
computer monitor in her car so she could return it. She had a
better idea about what she should get me for my birthday then
that.

That weekend she went out of her way to be a tease. She
would flash me her fanny and more of her breasts then she
usually exposed and at night she would eagerly engage in
fourplay, but we didn’t seem to ever get around to having
sex. She wanted me to be as fustrated and horny as she could
make me when my birthday came.
The same thing continued to happen that Monday and Tuesday
and by Wednesday morning I had an almost permanent erection.
I was just finishing my cup of coffee before going to work
when she came into the kitchen and informed me that she had
called my work and told them that I was sick.
“In fact.” She said gleefully. “I told them that you
probably wouldn’t be in until next week.” Now it was my turn
to be suprised as she took my hands and pulled to my feet.
She led me into the spare bedroom, then told me take off all
of my clothes.

“I bought you several new outfits for your birthday.” She
said. Her playful attitude was contagious and I was starting
to have a good time just getting undressed. She took each
piece as I removed it, including my shoes and my watch. She
told me to wait where I was, then disappeared through the
doorway.

I didn’t know what to think when she returned empty handed,
but she didn’t give me much time to think about it because
she stood right in front of me and started to take off her
clothes as well. After slipping off her high heels she
slipped her hands under her dress and skillfully pushed her
pantyhose down off of her legs.

She left them laying on the floor by her feet as she did
the same with the pair of brightly flowered panties she was
wearing. Only instead of letting them fall to the floor she
made sure that they hadn’t goten turned inside out and then
she held them out in my direction.

“I thought you might like to wear some of my things!” She
said knowingly, then she added. “In fact I know that you
would like to wear them!” She stared at me while she
continued to hold her panties out for me to take.
Inside I was almost out of control at the prospect of her
dressing me up in her feminine garments, but I tried not to
let it show. “I don’t understand.” I said as I took her
panties into my hand.

She planted her hands on her hips, then narrowed her brow.
“Don’t you give me any of that crap!” She said sternly. “I
know all about you and I know that your nothing but a little
sissy at heart.” She swung her hips back and forth in an
exagerated feminine movement.
“And I also know all about your dressing up in girls
clothes!” She said matter of factly. This caused me to almost
go into shock and I stood and stared at her, not saying a
word. “Now, you be a good girl and do what I tell you to do
so I don’t have to punish you!” She said.

In a stern voice she outright ordered me into her panties.
“Now put those panties on right now!” She stamped her foot
just to make sure I knew she was serious. She wanted to jump
with excitment when she saw me hold her panties open and then
step into them, but she remained like she was as I pulled
them up my legs and passed my hips.

As soon as I had done that she unzipped her dress far
enough that she could pull her arms free. “After you put on
your bra your going to go into the bathroom and shave all
that hair off of your legs!” She said as she unfastened the
clasp so that the lace and satin bra slid down her arms.
Just like she had done with her panties she held it out. I
was still dazed as I gingerly took it from her. I pulled it
around me and hooked it together, then pulled the straps up
onto my sholders.

She stepped closer to me and started to adjust the straps
so it fit me. “I noticed you didn’t have any trouble getting
it fastened closed!” She said in a teasing voice. “You must
have had plenty of practice.”She added.

Once she was satisfied with how she had adjusted the straps
she pointed toward the bathroom. “Now go shave off all that
ugly hair.” She ordered, then she said. “Young ladies don’t
have body hair sprouting out all over like that!”

She knew that she had made the correct judgement about me
when she saw me start for the bathroom like she had ordered.
In truth she didn’t know how right she was because I became
very submissive when I was dressed.
Fifteen minutes later I was standing in front of her while
she examined me. I had shaved my legs like she said, but I
also shaved my chest, arms, armpits and had shaved around my
now small triangular pubic area.
“Very good!” She said after looking me over. “Your looking
more feminine already!” She said in an obvious attempt to
embarrass me and when she saw that she had made me blush her
confidence doubled.

“Go pick up the nylons I was wearing and put them on next!”
She said with a nod. I didn’t waste any time complying and
after my legs were encased in her nylons she made me put on
her high heels. In just a couple of minutes I was standing in
front of her again.

She let me stand like that for a little bit as she cupped
and carressed her firm naked breasts. “Hmm. I like telling
you what to do.” She coo’d in a sexy voice. “It makes my
nipples hard.” She added.
After a bit she lowered her hands to her sides and then
lifed her dress a couple of inches so the lacy hem of her
slip peeked out from under it.

“Do you like my pretty slip sissy?” She asked, using that
teasing tone of voice again. I told her that I liked it very
much. “You want to wear it don’t you panty-waist?” She
taunted.
Again I told her that she was correct. Hearing this she
dropped her dress down so the slip was no longer exposed.
“Then beg me to let you wear my slip sissy.” She told me. “I
want to hear just how much you want to wear it!”
I slowly got onto my knees so she was towering over me.
“Please, Kelly let me wear your slip,” I begged. “I love slips
and I’ve never worn one that had been worn by you first.” I
pulled my panties up so that my cock was clearly visable
under the front panel. I had been slowly getting harder and
harder and now it was pretty close to being fully erect.
“Just look at how hard my cock is from me just thinking a
about wearing your pretty slip. Please let me put it on and I
promise to do whatever you say. Please!” I begged.
She stood over me smiling for a little while, then she
nodded. “Ok, you may take it off of me and put it on sissy.”
She said, with a snicker. I gently reached up under her dress
and carefully pulled her slip down her legs and then held it
while she stepped out of it.
Once she had I eagerly slipped my feet into the waistband
and then pulled it up into place. The lacy hem came to just
above mid-thigh. “Oh you look so sexy in my bra, nylons,
panties and slip!” She said softly. “So sexy you make me wet.
My little sissy makes my pussy wet when he does what I tell
him to do!” She said in an authoritative voice.
“I’m glad you think I’m sexy,” I said meekly, then added.
“And I love it when you tell me what to do.” She smiled when
she heard me say that.

“Good,” she told me. “Because from now on I’m going to be
telling you exactly what to do. Understand?” She asked.I
lowered my head and then told her that I understood.
She pushed her dress down so it fell in a circular ring
around her feet. Daintily she stepped out of the center of
it. She told me to pull it up into place but added that I
shouldn’t zip it closed just yet. I worked the dress up over
my hips, I had to tuck my slip back down afterward, then held
it tightly around my middle.

Kelly had busied herself with something in a box, but now
she turned so she was facing me again. “These are what I got
you for your birthday sissy!” She said, holding out a pair of
silicone breast forms. They were so realistic that they
jiggled like jello whenever she moved her hands.
I felt them for a minute as I thanked her and after she
handed them to me she pored a thick layer of super-glue on
the back of each one. “You know what I want you to do.” She
said as she snickered.

“I want you to push those breasts into place so they will
be permanently glued to your chest.” She reached out and
pulled the straps of my bra down off of my shoulders, then
pushed the satin and lace cups so they were forced a couple
of inches lower then they would normally be.
“Come on sissy.” She ordered sternly. “Glue those titties
to your chest. I know you want to!” I slowly raised both
breast forms up toward my chest. “That’s a good girl,” Kelly
said to urge me on. When they were about an inch away from
where my own breasts would be, if I had any, Kelly placed her
spread hands on the nipple side of each one.
With increasing pressure she pushed them closer and closer
until they were being firmly crushed aginst me. It only took
a second for the super-glue to set. She pulled my hands away
along with hers. I felt the expensive silicon breasts pull at
my chest as they were allowed to hang freely on thier own.
She began to knead them with her fingers. “I don’t know how
you would ever get them to come off.” She said happily. “But
that’s ok, because this is how I want you to look.” She
ordered me to pull my bra back up and then gave me permission
to zip up my dress.

Once it was securly fastened closed Kelly stepped back and
looked me over. She was now naked and I was wearing what she
had been wearing just a short time ago. She spread her feet
to about sholder width.
“I’m going to put make-up on you because I want to make you
into as much of a woman as I can. But now while your still
obviously nothing more then a sissyfied male I want to watch
you eat my pussy.” She said forcing me to my knee’s.
“I can always remember what you looked like right now,
because your never going to look this masculine again!” She
added as she pulled my face tightly aginst her wet crotch.
It only took a minute or so before she was grinding her
pussy into my face. She continued to hump me like that
through two climax’s, then she pushed me away.
“Go put on your make-up sissy so that there is nothing to
remind me that you were once a male.” She yelled. “I don’t
want to think of you in any way execpt that you are a woman.”
Without uttering a sound I went into the bathroom and made my
face up so that the illusion of me being female was complete.
Before going back into the bedroom I teased and brushed my
hair into a feminine style.
I stepped in front of her and curtsied. “Thank you for
making me into a female.” I told her. “What can I do to repay
you?” I asked from by still bowed position.

Kelly snickered and then pointed toward the foot of the bed.
“You can bend over that footboard and let me be the first to
use you like a woman would be used.” She said. I rose and
then bent over the footboard. The upper edge hit me right at
my hips.

“Get that dress out of my way and lower your panties
bitch!” She ordered. I pulled my dress and slip up onto my
back and then lowered my panties to the tops of my thighs.
Seconds later I gasped when I felt a blunt object press
against my tiny hole.
I snuck a peek behind me and saw that she was wearing a
strap-on dildo. “Oh your so small compaired to my big cock.”
She teased. “Are you sure you want me to take your virginity
bitch?” She jokingly asked.
“Please. Make me feel like a real woman.” I told her. “Take
me, use me.” She didn’t hesitate at all. She thrust her hips
forward so that the head of her thick cock was driven right
past my virgin opening.

The pain was so intense my legs gave out, allowing all my
weight to fall onto the footboard as I shreaked loudly. “You
already sound like a woman!” SHe snarled as she thrust her
pelvis forward a second time.

Again I cried out from the pain and I almost passed out.
Gasping several deep breaths I started to beg her to stay
where she was until I got used to having her cock inside me.
Her response was to ram her hips forward a third time. She
kept applying more pressure until her hips were pressing
firmly into my ass cheeks. “You took all of me cunt!” She
rudely told me. “I love the way you look bent over like you
are and with my cock buried as deep as it can go into your
pussy!”

I felt her grab my hips with her hands. “Now I’m going to
show you what it feels like when you get a good hard
fucking!” I was gasping and pleading with her to be more
gentle as she moved her hips away from me so her cock was
withdrawn from my tummy.

But all of that stopped when she slammed it back into me,
sinking all the way in with the one thrust. My legs were
convulsing and my inner thighs felt as if they had been
slashed with a sharp knife, but the stabbing, searing pain
flooding out from my violated hole into my groin and cock was
all I really felt.

Several more times she plowed into me like that, which left
me laying under her like a limp rag. I was slipping in and
out of reality as she started to steadily pump her cock in
and out of my once virgin pussy. I regained my sense’s and
was greated by the still painful sensation of her rythmic
fucking.

“Oh you take it good bitch!” She moaned. “Your so nice and
tight, just the way I like them.” She added. I felt her sink
all the way into me and then hesitate for a moment, but then
she picked right back up with the same ferious tempo. Several
more times she hesitated like she did before.
I was still finding it hard to move my legs and I moaned
when I felt her take my cock into her hand. She bent it back
between my thighs and then pulled my panties back up where
they belonged so that the crotchband kept it like that. I
could only gasp when she began to use both hands to stroke
along the narrow strip of my panties that passed between my
legs.

She knew how to make the smooth nylon move over my
imprisoned cock so that in less then sixty seconds I was
almost ready to squirt my come right into my own panties. She
sensed how close I was and she started to give my swollen
cockhead a good working over.
“Come on bitch!” She yelled. “Come in your panties for me!”

She forced the head of my cock down between my cheeks. “Show
me how much of a slut you really are cunt!” She shouted.A
couple of strokes later she began to spank my ass cheeks with
her open hand right through my panties.
“I ordered you to come you little slut!” She said swatting
me even harder then she had been. She wrapped her fingers
around my shaft as far as my panties would allow, then she
started stroking me from the front of my panites to back over
the head.
She saw my inner thighs tense up right before my hot sticky
fluid started to shoot out of my cock. That gave her time to
slip one hand under the waistband and shove her fingers in
front of my cock. This allowed her to catch every squirt on
her fingers, which she proptly shoved into my well fucked
hole.

In this manor, she managed to force my pussy to be filled
with my own sticky sperm. “Oh sissy!” She gasped. “I got hot
thinking about your own come being forced into your pussy!”

She said as she pulled my panties back down to my thighs. “So
I’m going to have to fuck you again!” She said with a laugh.
“Oh god, you’ll kill me!” I cried out meekly, but I was
surprised at how easily she sank into me.

“Your come makes a good lubrication bitch, just like all
women’s pussy’s are suppost to do.” This time I actually felt
myself pushing back to meet her forward thrusts.

“Oh Kelly, fuck me.” I begged. “Fuck my pussy good, fuck
my pussy hard!” I gasped.
“You can count on it slut!” She gleefully told me. “You can
count on it.”


sissy training videos

Last Updated on