A Very Sissy Love Story

January 15, 2011

“Mike,” He began, “I want you to be my Little Missy, if you want to be. Now, before you answer, let me explain a few things to you. If you agree, you will be bound and gagged whenever I choose. I wasn’t sure about the lingerie, but find I love it on you, and will be buying some outfits of your very own. I want you to understand that you will wear what I want, when I want. I also want to tell you now that you WILL be spanked. Not because you deserve it, but because it turns me on. I will punish you, bind and gag you, dress you like my personal Barbie doll, humiliate you, and degrade you. But most of all, I will love you. Now, I’m going to give you while to think about the whole idea.” He then directed me to remove the lingerie, and put my boy clothes back on. “I don’t want your thinking colored by anything. This is something that you have to really think about. Think about how you felt when we were kissing, when you were sucking my cock, but also, think about being helpless, truly helpless, and thinking you were going to be hurt. I’m going to go into the bedroom and read for a while, let you sit here and think. It’s now five after six. Say, I give you until six thirty? At that time, you can pick up the panties, bra, and the peignoir, leave, and there will be no hard feelings, and I will understand completely. Or you can put them back on, along with your little socks and heels, and come into the bedroom. It is your choice, Mike, but remember, it is an all or nothing choice.”


A Very Sissy Love Story

by: Missy Satinpanties

I guess I’ve always been bisexual, if not completely gay. I mean, in
high school, I lusted after the right girls, and wanted to get into
their panties like every other boy, but when I looked at the porno mags
we had, I always gravitated towards the girls who looked kind of
innocent, and were wearing soft, lacy lingerie. And yeah, I did wonder
how all that soft, slippery lingerie felt. A naked girl really didn’t
grab my attention, at all. And, if there was a picture of a guy getting
ready to have sex with some hot chick, I also quietly, but thoroughly,
checked him out. At first, there was no fixed idea in my head that I
wanted to have sex with a man, but that came on strong later.

My first experience with a man came in High School as a member of the
swim team, and it changed my life totally. I was sixteen years old,
would turn seventeen in January. Because of when I started school, and
the fact that I took some courses at the local community college, this
could be my last year in high school if I wanted to graduate early. On
the swim team, I was the guy who never won, but could usually be counted
on for a third or maybe a second, and a few points. I really wanted to
do better, and asked for some help. The assistant coach asked me to
stay after practice one chilly Friday in November Friday in order to
work on my stroke. He had me swim a length, and he would criticize and
correct, I would swim another length, he would again correct. Finally,
Coach Norton jumped into the pool to try to work on my kick. He had me
hold onto the gutter, while he manipulated my legs. His hands on my
thighs brought about a reaction that I usually reserved for glossy porn
magazines. After a few minutes, he “accidentally” brushed my crotch,
and made some joke about the bulge. He brushed my crotch at least 4
more times, each time moving his hand a bit slower. When I didn’t
object, he got much bolder, and cupped my erection through the thin
nylon Speedo suit.

Just a few minutes later found me naked in the trainer’s room, lying on
the padded table with Coach Norton giving me my very first blow-job! I
was in heaven as he kissed and licked my balls, ran his tongue up my
shaft, and then took me into his mouth. I came almost immediately and
also felt very guilty. We both dressed, silently, and then Coach Norton
and I talked about what had happened, and we both finally agreed we
wanted it to happen again.

Each Friday, I stayed late at the pool, working with Coach Norton, and
while my stroke did get better, it was the sessions in the training room
that really saw my “stroke” increase. The first few times, I was just a
passive recipient, but the third week, I became an active participant.
On the table that night, my right hand seemed to move on its own, and
gently cupped the coach’s balls. I ran my hand up and down his shaft,
feeling the heat radiating from his cock, feeling it grow in my hand. I
looked into Coach’s eyes, and he just nodded. I slid from the table,
and dropped to my knees in front of him. I just stared at my first
cock, and then slowly wet my lips and took the head into my mouth. As
soon as I did that, a switch seemed to go off in my head, and I pushed
forward, wanting to swallow as much of this cock as I could. After much
gagging and adjusting, this wonderfully warm, hard cock was sliding in
and out of my mouth. Coach Norton held my held gently, caressing my
hair, and giving me encouragement. I felt his cock swell in my mouth,
and instead of caressing my head, he grabbed it, forced his cock down my
throat, and filled my mouth and throat with his cum. Afterwards, he
gently lifted me to my feet, and then kissed me on the lips. I wasn’t
sure about this, but within seconds, my arms were around his neck, and I
was eagerly kissing this man, finally setting in concrete the fact that
I wasn’t bi, I was very gay.

The next Friday saw a shift in our pattern. During the week, I thought
about our encounters, that hard cock in my mouth, and that kiss. I
thought a lot about that kiss. While he was holding my head, and then
when he stood me up and kissed me. I felt so…well…like a girl. I
felt submissive and girly, At Thursday’s practice, Coach Norton
casually, but quietly asked me if I wanted to go to his house after
practice the next night. He asked me in passing, and about 5 minutes
later, I told him yes. That night, I gave my mom a BS story about where
I would be, and spent all day Friday with a hard-on and barely paid
attention to the world around me. Once in the locker room after school
though, we were told that something was broke and the pool heater was
dead, so no practice. Our head coach left for home, and Coach Norton
asked me if I would help him move some things in the office. The rest
of the team left, and after being sure that we were alone, I went out
the front door to my car, while Coach Norton went out the back and got
his. As I slid into my old Civic and pulled out to follow him, I had
the feeling that a whole new chapter in my life was about to open!

I knew that Coach was divorced, and that he had a 19 year old daughter
who graduated last year. I also knew that he taught the advanced
computer programming class, along with a few general computer courses at
the school. That was really all I knew about him. We got to his house
after about 20 minutes, pulled both cars into the garage, and got out.
He unlocked the kitchen door, and again, without any talking, he held
the door for me, and we went inside. Once inside, he gave me a kiss on
the cheek, and asked me if I wanted a tour of the house. It wasn’t a
large house, but it was nicely decorated with a big flat screen TV,
large comfy leather chairs, and a sofa in the living room, and a small,
but very tidy kitchen with a small table and 4 chairs. Next, he showed
me his neat and tidy bedroom, and then his daughter’s room, or at least
the room his daughter used when she was here. It turned out that she
was here every other month or so, when she wasn’t in school. It was
also the room she grew up in. Unlike the rest of the house, though,
tidy was not the word to use here. Posters were stuck up on the wall in
a chaotic fashion, and even though she had not been there in weeks,
there was a pair of jeans draped over the chair, and various pots and
tubes of makeup spread across the top of the dresser, and the bed was a
rumpled mess. But, what seemed to catch my eyes was a pair of pale blue
panties draped casually over the bed post. I wanted to touch them, to
feel them, to sniff them, so badly.

We then went back out to the kitchen, where he ordered a pizza to be
delivered, and then poured 2 glasses of red wine. He told me that if I
didn’t like it, he had soda, also. I tasted the wine, and found it dry
and it kind of made my mouth pucker, but I told him it was fine, and by
the time the pizza arrived, and I had been though 2 glasses, it was very
good. During the time we spent waiting for the pizza, we talked. We
talked about swimming, his daughter, the house, and finally, about us.
I admitted to really enjoying my first blow job, but that what had
really sent me into orbit was how submissive and feminine I had felt
when he held my head and forced his cock to the back of my throat,
picked me up, and then kissed me. I blushed, and told him I wanted to
be his little girl.

Coach just laughed, “I don’t want a girl, I want you! But, maybe you
could be my little sissy?” “What do you mean,” I asked. “Finish your
dinner, and I’ll show you,” he replied. Soon, we were done with the
dishes in the sink, and without another word, he lead me to the living
room. “Now, Mike,” he began, “I have been thinking of this night now
for a month, and I want to know if you are willing to go along with my
little fantasy. I think I can make a few small changes, to what I was
planning, and that will make us both be very happy. Shall I explain?”
Eagerly I told him to go on! “Okay.” He began, “I’m gay, and like to be
in control, and since you have told me you like being submissive, that
should work, right?” I nodded my head, not really sure where he was
going with this. “I want to make love to you while you are tied up and
gagged, do you understand? I thought for a moment, swallowed, and
slowly told him to go on. I think the bulge in my pants would have
answered for me if I hadn’t said anything, though. He then took me by
the shoulders, kissed me gently on the lips, and told me to take off all
of my clothes. Even though it was warm in the house, I began to shiver
as I slowly removed my pants and shirt, as though I had no will of my

Once I had all my clothes off, Coach just looked me up and down. Here I
was, a skinny kid with longish hair, but barely any hair on the rest of
my body, and a stiff cock, standing naked in a man’s living room,
knowing, or at least thinking I knew, what was coming next. Coach
reached out, and took my hand, looked me in the eyes and gently told me
to call him Tom, and then led me to his daughter’s room. There, he told
me to sit on the bed, while he rummaged around in the dresser, and then
in a large box on the floor of the closet. While he was rummaging, I
picked up those soft panties, and ran them through my fingers, and
across my cheek. They were heavenly! Finally, with a triumphant,
“Aha!” he stood up, and turned around. I quickly dropped his daughter’s
panties, hoping he hadn’t seen me. “These things were my daughter’s
when she was about 12 or 13, and they should fit you nicely. The last
time she was here, we went through her stuff and threw out a lot, and
this box was to go to the dump, too, I just never got around to it. He
then held out his hands, and showed me what he had found. I was staring
at a pair of pale yellow satin panties, with ruffles around the leg
openings made of the same material, and three rows of white lace across
the bum. He also had a matching bra, with some lacy touches, and a
little white satin bow in the front. He laid these on the dresser, as
he explained further. “My daughter was in a state fair pageant, and
this was one of the outfits that she wore. Instead of swim suit and
evening gown, they did swim suit and fancy square dance costumes. I
think these should just about be perfect for a little sissy like you.”
He smiled, blew me a kiss, and went back to rooting in the closet. He
stood up a moment later with a pair of white high heels, set them on the
dresser, and then dove back into the box, and pulled out a pair of
little white nylon ankle socks with a cloud of yellow lace trim around
the top.

I stood up, and moved across the room in a daze. I picked up the
delicate satin panties, and ran my hand over the soft material, then
rubbed them against my face. “Would you like to try them on?” Coach, I
mean Tom asked gently. Again, in a daze, I could only nod my head. I
sat down on the bed, and slid those soft, heavenly, and feminine panties
up my legs. I stood up again, and pulled them up around my waist,
reveling in the tight softness around my waist. Tom then came to me,
and told me to hold my arms out. He slid the bra up my arms, turned me
around, and fastened the catch at the back. I was now wearing a bra and
panties that really looked better suited to a 6 year old in one of those
beauty pageants you see in the documentaries on the Discovery Channel.
Tom asked me to sit back down and told me to point my left foot, and
slid a slippery nylon anklet and a shiny white, high-heeled shoe on my
foot, and then buckled a little strap across my instep. He repeated the
process with my right foot, and then helped me to stand. The shoes had
rounded toes, and looked like the black shoes that a little girl would
wear. Mary Janes, I think they’re called. They were rather tight, and
even though the heel was only about 3 inches tall, I could only stagger
instead of walk in them. Now, Tom handed me a sheer white robe that he
said had belonged to his wife, and was not designed to conceal anything,
or to keep you warm, I decided quickly.

After I practiced walking a bit, and could navigate without falling
down, Tom took me by the hand again and led me out into the hallway, and
then to his bedroom. As I made my way to his room, I was aware of the
bra straps digging into my shoulders, the ruffles around the legs of my
panties tickling my thighs, the soft panties as they rubbed against my
bum, the tight, restrictive shoes, and the diaphanous gown floating over
all. I think I was walking two feet above the carpet. While I stood at
the foot of his bed, he went into his own closet, and brought out a box.
“I hope you like these, Mike, I bought this all especially for you, not
even knowing if you would consent to wear it for me.” He said. “But,
you know, we have a little problem,” he went on,” I can’t call a cute
little sissy like you Mike anymore, can I? I think maybe Michelle, or
“Missy” for short would be a good name, what do you think?” I nodded
eagerly, and looked at the box to see what kind of goodies he had for
me. The first item looked like a pair of white mittens. In fact, they
looked exactly like a pair of white satin mittens, with no thumbs. He
took each hand, told me to hold my fingers together, and slid each
mitten on my hands, and then buckled them onto my wrists, with what
looked like two white leather straps from a lady’s watch. I now found
that there was a layer of thick material between the inner and outer
layer of satin, which made my hands completely useless. There was also
a shiny silver hook on each one that confused me as to what they were
for. I was soon to learn. Next, Tom brought out a white patent leather
collar with white lace trim top and bottom. This he buckled around my
neck, not tight enough to hurt, but I knew it was there. Finally, he
took each hand, and brought it up to my neck, and then I knew what the
hooks were for, as he fastened each wrist to a ring at about the seven
and five o’clock position (assuming the front of the collar is the
twelve o’clock position) I was now in lacy little girly lingerie, heels,
with my hands immobilized in satin mittens, buckled to a collar around
my neck. I was scared to death, excited, and curious, all at once. But
most of all, I was turned on.

Tom gently took my face in his hands, and kissed me on the forehead. He
told me that if anything happened that I didn’t want to happen, I was to
either say the number three, snap my fingers three times (In these
mittens??), or stomp my foot three times, and everything would stop. As
he held me, I told him I understood, but really, could think of nothing
except that I was now a 15 year-old sexual object, here to fulfill this
man’s sexual desires, and it was all out of my hands. I was helpless,
submissive, and never wanted this to stop, no matter what happened next.

He began to kiss me, first on the forehead, the light little kisses on
my eyelids, and cheeks, finally kissing my lips. At first, they were
gentle little kisses, but then they got more urgent, until finally he
was holding my head, and pressing his lips hard against mine, his tongue
exploring my mouth. I almost passed out with the pleasure of it all. He
stepped back, and slowly took his shirt off, revealing his strong,
hairless chest and stomach. Ever so slowly, he kicked off his shoes,
and lowered his pants, now just standing in front of me in a pair of
black cotton bikini underwear. I could see his cock bulging the front
of the bikinis, and thought about this thick, 8 inch cock, and how good
it felt in my mouth. Tom walked over to the bed, and came back with a
pillow, which he placed on the floor in front of his feet. Slowly, but
firmly, he placed his hands on my shoulders, and pushed me down, until I
was kneeling on the pillow.

“Missy,” he began, “You are now mine. You are my lover, you are my
slave, you are my slut!” Show me how much you love me, and kiss my cock
through my underwear!” Earnestly, I began to kiss and lick him through
the cotton, kissing the skin of his thighs, and nuzzling his crotch,
inhaling his musk. After a few minutes of this, he lowered his bikinis,
and his erect cock sprung up and slapped my chin. Without any
direction, I began to kiss his cock, and to lick the shaft and his
balls, using my tongue and lips with all the skill and passion I could
muster. I took the fat, purple head into my mouth, and swirled my
tongue around it, and then began to suck as hard as I could, releasing,
and then sucking, each time taking a bit more of that wonderful cock
into my mouth. When my face was jammed against his stomach, he took my
head in his hands, but this time, instead of holding me, and fucking my
mouth, he pushed my head away. I just looked up, and asked him what was

Tom didn’t answer me, just took my arms, and stood me up on those
unsteady heels. Kissing me again, he told me to stand very still, and
not look around. He went to the box again, and took something out. I
felt his hand on my ankle, as he told me to spread my legs. A cuff of
some kind was wrapped around first my left, then my right ankle, and
then something was clipped onto the cuffs. “What I’ve put on you, Missy
dear, is a spreader bar, that forces you to keep your legs spread.” I
had no idea of why he wanted to do that, but I have to admit to really
being turned on by the whole scene of being feminized, and completely
helpless. Well, not completely I guess. I mean, I could still use the
safe word, tell him to stop, scream for help, I suppose, if I really had
to. He was now standing behind me, stroking my hair, running his hands
over my butt, and stroking my nipples through the yellow satin bra. I
had never known how sensitive a boy’s nipples were, but what he was
doing felt sooo good! He would gently pinch and twist them, then stroke
them, and I never wanted him to stop! Next, he moved his left hand up
to my face, and began to stroke my cheek. His finger went into my
mouth, and I began to suck on it, Then, he put a second, and a third
finger in my mouth, and gently pried it open. As he did this, he
brought his right hand around and forced something large and kinda soft
into my mouth. Quickly, he grabbed the straps that dangled from this
thing, and buckled them tightly behind my head. I was now bound and
gagged, in lingerie, with my legs held open. I was scared! While my
tongue explored this intruder, Tom came around in front of me, and told
me that I now had a rubber, penis shaped gag in my mouth, and he could
do whatever he wanted to me, as I could neither yell out, run away, or
use my hands. I was getting more scared by the moment. He then told me
he could whip me, use a cane, or do whatever he wanted, as I was his
slave. Now, I was crying!

Tom began to laugh, and told me not to cry. “Isn’t this what you
wanted, Sweetheart?” he asked me softly. You wanted to be a helpless
little sissy-boy, and I have wanted a submissive little boy for so-o-o
long! But don’t worry; none of those terrible things will happen to
you, at least not tonight!” With that, he unhooked my wrists and
ankles, and then unbuckled and removed the gag from my aching jaws.

With that, he took me into his arms, and hugged and kissed me,
stroking my hair, and nuzzling my neck. I was very confused, but could
only respond to his loving ministrations. After a few, too few,
minutes, he held my shoulders at arm’s length, and told me wanted to
talk, seriously, for a moment. After removing my satin mittens and the
leg spreader, he took hold of my hand, and we went back out to the
kitchen, with me still toddling awkwardly on my heels.

He sat me down at the table, and busied himself making some coffee. When
it was ready, he asked me how I liked mine, made us each a cup, and sat
down opposite me. “Mike,” He began, “I want you to be my Little Missy,
if you want to be. Now, before you answer, let me explain a few things
to you. If you agree, you will be bound and gagged whenever I choose.
I wasn’t sure about the lingerie, but find I love it on you, and will be
buying some outfits of your very own. I want you to understand that you
will wear what I want, when I want. I also want to tell you now that
you WILL be spanked. Not because you deserve it, but because it turns
me on. I will punish you, bind and gag you, dress you like my personal
Barbie doll, humiliate you, and degrade you. But most of all, I will
love you. Now, I’m going to give you while to think about the whole
idea.” He then directed me to remove the lingerie, and put my boy
clothes back on. “I don’t want your thinking colored by anything. This
is something that you have to really think about. Think about how you
felt when we were kissing, when you were sucking my cock, but also,
think about being helpless, truly helpless, and thinking you were going
to be hurt. I’m going to go into the bedroom and read for a while, let
you sit here and think. It’s now five after six. Say, I give you until
six thirty? At that time, you can pick up the panties, bra, and the
peignoir, leave, and there will be no hard feelings, and I will
understand completely. Or you can put them back on, along with your
little socks and heels, and come into the bedroom. It is your choice,
Mike, but remember, it is an all or nothing choice.”

I sat there for a few minutes, sipping at the coffee, and thinking. I
ran my hands across my jeans, feeling the rough material, and
contrasting that to the delicate softness of the satin panties that were
sitting on the counter, and which had so very recently covered my little
sissy bottom. I thought about the panic that I had felt when Tom told
me I could be caned, or beaten, and could do nothing about it. I
thought of the pain in my jaw from the gag, the soreness from the tight
shoes, and of having my wrists pinned to a collar around my neck, and
weighed all of this against the softness of the panties, and made my


Tom heard the door to the garage open and close within about 5 minutes
of leaving the kitchen, and he sighed. “My Missy is gone,” he thought to
himself. Mike was such a beautiful boy, and the thought of him
restrained and dressed in sissy lingerie made him so hungry. But, he
knew the decision was Mike’s, and while he hated the choice, he had to
respect it. He just sat there on his bed, an unread magazine in his
lap, and a glass dark with whiskey in his hand. He sat there for
another ten minutes or so, and was just going to get up, and put the
coffee cups in the dishwasher, straighten up the kitchen, and watch some
television, when he heard the garage door open and close again. He
listened, wondering whether he should call 9-1-1, or what he should do,
when he heard a wonderful sound.

The sound of high heels clicking on a tile floor carried clearly though
the house, and then the bedroom door opened, and Mike, his own dear
Missy, was standing there in his new lingerie and heels, smiling shyly
at the older man. Setting his glass down with shaky hands, he started
to get up, but just sat there, not daring to move, lest this vision of
loveliness disappear again.


I had indeed made my decision, and made it quickly. I had stepped
out into the garage to privately practice walking in these shoes a
little bit. Now, I walked, no, I minced, over to Tom, and knelt down
beside him, draped myself over his knees, smiled up at the confused man,
told him I was ready for my first spanking.

Tom’s hand landed again and again on my poor pantied bottom, and I
squirmed and wiggled, trying to avoid each smack. After about 20, not
very hard smacks with his bare hand, I was crying and trying to get my
hands over my sore bottom. Tom had grabbed my arms, and held my wrists
together in one hand, while he delivered a few more blows, and then it
was all over. He stood me up, and held me like a lover. I wrapped my
arms around his neck, and whispered in his ear that I was his Missy,

We ended up in bed, cuddling and kissing for the longest time, and then
worked our way into a 69 position, and brought each other off. I didn’t
want his dick out of my mouth, I wanted to hold it there, forever, but
all good things must end, and it was soon time to take a shower, and go
home. As I was getting dried off, Tom brought me a little present.

He handed me a small, blue rubber object that I soon learned was a
beginner sized butt plug. “Now, Missy, I want you to wear this at least
one hour a day, for the next two weeks. If you can, leave it in for two
or three hours, but no more than that. When you take it out, wash it in
hot soapy water, dry it off, and hide it.” Then he handed me a small
bottle of Astro Glide, and told me that it was a lube to use with the
plug, and to make sure no one saw it, either. Finally, he handed me a
pair of pale blue nylon panties, with lace panels on either side of the
front. I looked at the label, and saw they were Victoria’s Secret
brand. They looked expensive and very pretty. “Missy,” He said, “These
are for you to wear when you come over a week from next Saturday. I
have to go out of town next weekend, so it will be two weeks until I see
you again here. Now pay close attention. You WILL be here no later
than nine o’clock, and no earlier than five minutes of nine. You will
wear those panties and your new butt plug under your clothing. You will
walk around to the back of the house, where you will find a set of
instructions. Follow them exactly, and you will not be punished. Make
a mistake, and you will be punished. Is that clear?” I told him it
was very clear, and he kissed me long and hard, and then told me to get
going. That Saturday was a long, long. long-g-g-g way off.

I tried the new plug that very night, and realized that it was going to
take some effort. I tried several different angles of insertion, and
several different positions, until I found that if I lay down on my
back, and lifted one leg high, I could get an angle that allowed me to
get it passed my sphincter. Getting is past without pain was another
thing, and I finally understood that it was going to hurt, gritted my
teeth, and pushed it home. I almost yelled out with the sudden pain,
but managed to keep quiet. It felt alien, and even though the fat part
was inside of me, it still hurt, and gave me a burning sensation. I
managed to leave it in for about fifteen minutes, then with another
burst of pain, pulled it out, smuggled it into the bathroom, cleaned it
up, and hid it in the toe of a pair of dress shoes I hardly ever wore,
with the lube in the other shoe. The panties went into a lidded,
tankard-style mug that sat high on a shelf, and was only moved to dust.

Each night, I would get home from swim practice, frustrated because I
was so close to my, well, what I now thought of as My Loving Master, but
could say or do nothing. As soon as dinner was over, I would rush to
my room, race through my homework, put on my pajamas, and insert the
plug. By Wednesday evening, I could get it in without pain, and on
Thursday, I put it in right after dinner, did my homework wearing it
(although the hard wooden chair pushing on it felt funny), and then left
it in while I sat downstairs watching TV with my parents. That was
kinda weird, but neither of them could read minds, so I was safe.

Finally, it was Saturday. And I mean it was the Saturday! I woke up
early, and took a long, hot shower, using some of my younger sister’s
flower scented shampoo to wash and re-wash my hair, and one of my
mother’s razors to remove what little bit of hair was on my legs, my
underarms and after some trepidation, the sparse hairs on my crotch and
my balls. After I got out, and my hair was dry, I brushed it until it
shone, and went back to my room to finish getting ready. I had already
told my Mom another story about where I would be, so that was covered.
My dad had left us, although he sent a fat check every Friday, so no
problems there. Mom had taken my sister to the church to practice for
the Christmas pageant, so no one was around to comment on my washed and
brushed hair, or the quick spritz of my sister’s perfume, which was the
same flowery scent as the shampoo. I jumped in my 12 year old Honda,
and left home for Heaven.

I sat around the corner, studying my watch. When it was exactly 4
minutes of nine, I drove up the drive, and walked around to the back.
There, I found a small box and a note. It read: Missy, as soon as you
get this note, ring the doorbell, once. then, reach into the box, and
take out the towel that you find, and place it on the step. Take off
all of your boy clothes, put them in the box, and stand there, in just
your pretty panties and plug. Shivering in the early December cold, I
stood there, hoping no one would see me, and hoping the door would open
soon. I needn’t have worried, because I only stood there for less than
a minute, before the door swung open, and Tom stood there in a black
kimono and slippers, smiling down on me.

He reached out, and lifted me up, swung me into the kitchen, and into
his embrace. We stood there, kissing like long lost lovers for what
seemed like an hour, but was really only a few minutes. I felt so warm,
loved, and needed. I was ready to do whatever this lovely man wanted me
to do. Finally breaking our embrace, Tom reached over to the counter,
and handed me a pink satin robe, and a pair of soft pink slippers. I
slipped then on, and sat down at the table with him, and enjoyed a cup
of coffee and some chit-chat. I have to tell you, that I felt like
nothing other than his loving wife at this point, a feeling that I never
wanted to go away. He finally told me that he had a surprise for me,
no, several surprises, actually.

“First of all, my little sissy lover, since we last met, I have been on
the internet, and have spent quite a bit of money on some clothing and
some, toys for my little love.” I blushed, and stammered thank you. He
continued, “I think you will love most of what I have bought, and will
come to love the rest. I also want you to know that before this weekend
is through, you and your cute little ass will be in for huge surprise!”
At that, I know I turned a bright red, and could only stare at the
floor. This was going very fast, and even though I wanted to do this,
it was still so very new to me. Also, I had brought up to believe that
someone who was gay was somehow less of a person, someone to ridicule
and belittle, yet here I was, falling in love with a gay man, dressing
like a girl for him, and being gay myself. I was so conflicted,
thinking one thing when I was dressed in jeans and a flannel shirt and
with my friends, but thinking completely different thoughts when I was
laying on my bed, a butt plug inserted in my bottom, and my hand wrapped
around my young cock. Finally, I looked up at Tom, my face warm, and
told him, “Tom, I am yours and yours completely. Whatever you want to
do and whatever you want me to wear is okay with me. If you are happy
and satisfied, then so am I. I just want to be with you, to feel your
body next to mine, and to love you.”

With that, Tom just beamed a 500 watt smile across the table, and told
me that from now on, I was not to call him Tom, or Coach, unless we were
in school. From now on, I was to refer to him as either “Daddy”, or
“Sir.” I would know when to use which name, he was sure. “Yes Daddy,”
I replied, grinning. “Now, come with me to your new bedroom,” Daddy
told me, and we got up and walked hand-in-hand to the spare room. There
was a deadbolt lock on the door, and as he opened it, I just stood there
and gasped out loud. Instead of the bland spare room I had seen just
weeks ago, there was now a perfect girly-girl’s room! A white canopy
bed with pink satin coverlet, and sheer pink and white netting over the
top, white dresser and make-up table, and a pink rug in the center of
the room would surely win the heart of any prissy little girl, and it
certainly won mine!

He ushered me in, and opened the closet door, and again I gasped! There
was a frothy pink satin dress hanging there, along with another dress of
some kind in black satin, and at least three or four blouses and skirts.
On the floor were three pairs of heels, one shiny black with very high
heels, a pair of pink pumps, and the white heels that I had worn the
last time. He then opened the top drawer of the dresser to show me that
it was full of panties, all in soft satin, nylon, and the prettiest,
softest pastels. I just looked at this wonderful man, and all I could
say was, “I love you, Daddy, I love you so much!” With that, we were
back in each other’s arms, his face in my hair, stroking me though my
robe, and both of us crying for sheer joy. “I love you too, my little
sissy, I love you too,” was all he could say for several minutes.

We finally broke apart, and he told me that he had another surprise for
me, and that surprise would come after dinner that evening. Then, he
told me to sit down on the bed, and he would dress me for a little
“scene,” as he called it. I went to the bed, and sat down, not really
knowing what I was supposed to be doing. He walked over to me, and
knelt down in front of me. He removed my slippers, and told me to point
my left foot. I did so, and he rolled a delicate white stocking up my
leg. I shivered as the soft material encased my bare leg. After both
stockings were on, he slipped the white heels on my feet, and buckled
the little straps over the instep. He then told me to stand up, walk to
the foot of the bed, and stand facing it. I did, and he came up behind
me and slipped off my robe, and gently pulled my pretty panties down my
legs. Reluctantly, I stepped out of them, now standing in just hose and
heels, waiting to see what Daddy had in mind. He then went back to the
dresser, and pulled out something that was pale blue with a white lace
overlay, and had strings hanging from it. It took me second, but I soon
realized that this was a corset! I had seen them on women in the
magazines, but had never seen one “for real,” and never thought I would
be wearing one! He stood behind me and wrapped it around my waist,
pulling it snug. It was then back to the dresser, and this time it was
nylon wrist cuffs with Velcro closures. He wrapped them around each
wrist, and the clipped the cuffs to eye bolts I had missed, on each of
the bed posts. With that, he grabbed the lacings, and pulled them as
tight as he could, causing me to gasp that I couldn’t breathe! I was
told to breathe shallow, and to relax, as he pulled them even tighter,
and then tied off the strings behind my back. He knelt behind me, and
started kissing my bottom, and toying with the rubber ring of the plug
with his teeth. After a bit of this, he pulled my stocking tight, and
clipped them to the garter straps that hung down from the corset. Next,
he told me to pick up one foot, and then the other, as he slid my pretty
panties back up, and settled them on my butt. Out came the familiar
ankle cuffs, but this time, he didn’t attach the spreader bar. He took
my wrists, and unhooked them from the bed, and then hooked them together
behind my back. “Soon, Sweetheart, I will have you in an arm binder,
and will pull your little arms back until your elbows touch! But not
right away, and not this weekend, so you don’t have to worry your pretty
little head, yet,” He chuckled, but not in a pleasant way, and again, I
got those shivers of fear running up and down my back.

Now he lead my down the hall, and back into his room. It was dark, and
the only light came from about 20 candles burning around the room,
giving it a romantic feel. He told me to crawl up onto the bed, and
stay on my knees. With my hands behind my back, this was difficult, but
I finally got onto the bed. Now, he pushed my legs apart, and put the
spreader bar between my ankles. Coming around in front of me, he told
me to open my mouth, and close my eyes. I did so, and the penis shaped
gag filled my little mouth once more. I had no idea of what was coming,
and was scared, thrilled, worried, and not a little turned on! He
shoved a large, rolled up duvet in front of my knees, and pushed me down
onto it, My hands were cuffed behind my back, my legs were spread, and I
was gagged with my ass up in the air. I began to wonder what was
coming, when, WHAP! He landed three solid blows with a leather strap on
my unprepared bottom, causing me to scream into the gag, and try to jump
and move. No luck, as his other hand was on the small of my back,
making avoiding the smacks impossible. Three more slow and hard smacks
had me crying and screaming, although all he could hear was grunting and
muffled noises coming from me, and could feel my body heaving with the
sobs`. He finally quit, and pulled my pretty blue panties down off my
bottom, gripped the ring of the plug, and with a little pop, pulled it
out. In the last week, I had worn this plug a lot, and felt sort of
empty without it in my little sissy bottom. I needn’t have worried.

He gently probed my bottom hole with his finger, and then smeared more
lube up there. “Now Missy, this is probably going to hurt, so if you
want me to stop, just tell me, okay?” This line was delivered with
another lewd chuckle. “Oh, I’m sorry, you can’t tell me, can you?
Well, we’ll just have get over that, won’t we, Sweetie?” With those
words, I felt something hard at my bottom hole. He pushed and twisted,
and it hurt worse than when I first tried my beginner plug. “I’m
inserting a much bigger plug, now that you are used to that little
beginner’s toy. I really think you will like it!” Daddy now placed one
hand on the small of my back to hold me down, and gave my new plug a
very hard push. I screamed as loud as I could into the gag, tears
running freely down my cheeks, my feet kicking those few inches my
bondage would allow. I felt as though I couldn’t breathe because of the
gag and corset, and now my whole body was being split in two from this
huge (I thought) and impossible plug! “Hush, my Sweet Angel, and
breathe through your nose,” he advised. “Just relax, and soon, the pain
will go away. I used a light anesthetic cream with the lube, so the
pain shouldn’t be as bad as it sounds. At least I hope it doesn’t hurt
that badly!” He was right. After a few very, very painful and
torturous minutes, the pain subsided to a dull ache. Daddy must have
noticed that I had quit squirming, and was breathing easier, because he
began to stroke my back, and rub my bottom through the panties. Without
any conscious thought, my cock reacted, and was trying to rip a hole in
my new panties! He increased the pace of his strokes, now reaching
around to rub and tweak my nipples, poked out above my corset. I was
stiff, my jaw ached, and my bottom was still on fire from the spanking
and the plug, but I was as turned on as is humanly possible! Suddenly,
without any touching at all, I felt the bliss of orgasm, and spurted cum
into my panties.

I lay there, the intruder still in my aching backside, dressed in a
corset too tight to breathe in, gagged and bound, and I realized that
this is what I wanted. I wanted nothing more than to be completely
under another man’s control. I wanted to be told what to wear, where to
sit and stand, and when and how to have sex. I was in total submissive
sissy heaven! As these thoughts were crossing my mind, Daddy was
helping back up on my knees, and unlocking the spreader bar from my
ankles. He helped me off the bed, and I stood there on shaking legs,
wondering what was next. I didn’t have to wait long, as he unbuckled
and removed my gag, and the slid my cum filled panties down my legs. I
stepped out of them, and he brought them to my mouth, and told me to
lick my cum out. There I stood, still cuffed, and in a corset, heels,
and hose, licking my own cum from my panties, and loving it. After a
moment or two, he tossed the panties in the corner, and took off my
cuffs. He kissed me gently, and told me to take a bath, and remove the
plug in the tub. So a few minutes later, I was sitting in a perfumed
bath, with Daddy washing me with a soft washcloth, and together we
pulled the new plug out of my sore little behind. I was surprised at
how narrow it actually was. I had had visions of something the size of
a telephone pole up my backside, and this was just a bit bigger than my
thumb! “Don’t worry about it, Honey,” Daddy told me, “You’ll get used
to the feeling, and then, your Daddy will fill you with the real thing!”
I couldn’t wait!

He helped me out of the tub, and dried me with a soft pink towel, handed
me the pink robe that I worn earlier, and we walked back to my new
little girly room. I sat on the bed, and he sat on the little stool in
front of the make-up table.

“Remember when I told you about some clothing you may like, and some you
may not?” I nodded. “Well, what I’m about to show you may be in both
categories. He then went to the closet and produced a pink satin dress
that was the most beautiful thing I have ever seen. It had a peter pan
collar (although I didn’t know then what it was called), short capped
sleeves with a white satin bow on each sleeve, and was trimmed in white
lace. He laid this creation on the bed, and produced a little nylon top
that ended in a huge mass of ruffles. “This is a pettiskirt, and you
wear it under your pretty dress,” he explained. He then pulled out a
pair of little nylon anklets with pink lace, and black, patent leather
Mary Janes and laid them on the bed next to the rest of the outfit.
“Where are my panties, Daddy?” I asked. “Hmm, I think we will get to
those in a moment, okay?” He then helped be put on the socks and the
shoes, buckling them tightly onto my feet. He told me to lie back on
the bed, and to raise my legs. I did, not knowing what to expect. “Now
Missy, whatever I do, I want complete silence, or I will gag you for the
rest of the day and night, and you won’t get any dinner.” I resolved to
be silent, no matter what. He took my new plug, and after applying lots
of lube, pushed it into my backside. I thought it was a different plug,
as it didn’t hurt very much at all, but he told me it was the plug that
I thought was going to kill me just a short time ago. Now he took
something from under the bed, and slid it under my bottom. As he folded
the material over my crotch, I realized that he was putting me in a
diaper! I almost said something, but stopped just short. After pinning
it very tightly on me, he slipped a pair of plastic panties up over my
legs, and then I felt something strange. The waistband was pulled
tight, and I heard a loud click, as he told me that my plastic panties
were now locked on me, and would not come off. He followed this by
sliding on a pair of pink satin panties with lots of lace on the bum
that covered the pink plastic ones. I then stood up, and realized that
I could not bring my legs together as the diaper was way too thick!
Daddy then helped me pull the petticoats on, and I was amazed at how
they stood out from my waist, and at how short they were. Finally, it
was time for the dress. He floated it down over my head, and smoothed
it out over the petticoats, then went behind me and zipped it up. After
the zipper was up, I heard a little metallic click, and he told me that
I was now locked into my pretty new dress, too, and only he had the
keys. I told him that he also had the key to my heart, and got a soft
kiss on the cheek. I looked in the full length mirror, and saw a little
girl looking back at me. My satin and plastic covered diapers were on
full display under the too short skirt, and I wasn’t really sure about
where this all was going. I was determined, though, to ride this road
all the way to the end. I loved my Daddy, and I trusted him, and would
do whatever he wanted of me. The final touch was a matching satin baby
bonnet that he tied under my chin, and the satin mittens that again made
my hands useless lumps.

I took Daddy’s hand, or rather, he took mine, and I waddled into the
kitchen with him. He sat me down and asked me what I thought of the day
so far. I looked at the clock on the wall, and was surprised to see
that it was only just after one o’clock. So much had gone on, that I
was sure it was late evening! We talked for a long time, Daddy drinking
coffee, and me drinking apple juice from a plastic sippy cup. Daddy
told me I was so-o-o cute like that. I could only blush. I told Daddy
that I really didn’t like to be hurt, but it felt so good when he made
it feel better afterwards, that I didn’t mind it too much. This also
brought about the subject of the butt plug that was beginning to hurt as
I sat on this hard chair, even though the padding of the diaper. “You
have to get used to the feeling of something up your bottom, Dear One (I
loved his sweet names for me!),” he said. “When I finally make love to
you, I don’t want to hurt you, but then again, I don’t want you to be
too loose!” He laughed as said this last, and I chuckled along with him.
Finally, I got the courage to ask him why he dressed me as a baby. He
told me that a baby was the ultimate in dependent. A baby did not talk,
did not feed itself, could not use a toilet, and had to rely on his
parents for everything, and that since I wanted to be submissive, and
feminine, this was the pinnacle of sissiness. “And remember, little
one,” he went on, “you are mine to dress and to do with as I please. If
I want you as a baby girl, or as a French Maid, or hogtied naked in the
closet, that’s what will happen, do you really understand?” Again, it
felt as though I was being given an option to leave, and I sat there,
thinking about that for a long few moments. I put down my cup, and ran
my satin covered hands over my legs, then over the dress, feeling the
soft material, and hearing the rustle of the petticoats, and the soft
crinkle of the plastic panties. I stood up, and walked over to the
living room, and looked at myself in the mirror over the fireplace. I
was a boy, as my hard on seemed to prove, but I was standing in a man’s
living room, dressed in pink satin like a baby girl, willingly allowing
myself to be a slave, or play toy, or I really didn’t know what!

After a final glance in the mirror, I waddled back into the kitchen, and
sat down. I took a sip from my toddler’s cup, noticing the Winnie the
Pooh motif, set it down, and looked at my new Daddy, and then back down
at the table. “I know I’m young, and a lot of people would think I’m
too young to make such a decision, but I have made one, anyway.” I
started, “I have only really known you for a short while, and most of
that time has been spent with sexual pleasure. I thought at first, I
just wanted the sex, but I have really thought about it, and, Daddy, I
love you. I don’t love you as a father, but the way I think I would
feel about a girl that I wanted to be with. I am yours, and want to be
yours until you don’t want me anymore.” I looked up again to see Daddy
in tears. “I love you so much, little Missy! I’m so glad to hear that
you love me too! Now, I have just one question to ask you.”

I looked at him, sitting there in his black kimono, so masculine, and
then thought of me looking so sissy, and wondered what new question he
could ask me. I didn’t have long to wait. He stood up, came around the
table, and knelt down beside me. He reached into the pocket of his
robe, and brought out a small box. He opened it up,
displaying…displaying…Oh My God, an engagement ring! “Missy,” he
whispered, “Will you marry me? Will you be my bride? Will you be my
beautiful sissy bride?” I just sat there, stunned. My emotions
swirled around in my head colliding with questions about my family, my
future, our future, and on and on. I looked this wonderful man in the
eyes and said the only thing I could say, “Yes, I will marry you, and be
your sissy wife.”

He slipped a diamond solitaire ring on my finger, and we hugged and I
cried for the longest time. He led me back to his bedroom, where he
took off my locks and mittens, and helped me to change into a beautiful
peach silk baby doll nightie, and we crawled into his bed to talk. We
lay there, listening to Bach on the stereo, talking for hours. I
learned that he had been working on some application programs for a
popular piece of consumer electronic gear, and had sold three to the
company who made it, and for very good money indeed!. They, in turn,
offered him a job that was many times better paying than public school
teaching. Along with the money from the sale of his house (It was sold,
he was actually renting it until the end of the school year from the new
owners!), and what he had in the bank, we could afford to move out to
California, and when I was of age, we could married legally. For now,
we would have a private ceremony, and as he said, “Be married in our
hearts, if not in the law.” Finally, we came to the point where we had
to talk about my parents, and what and how to tell them. My parents
were getting a divorce, and my dad had already moved out, so really, all
that was left was to tell my mother, in such a way that she wouldn’t
freak out, call the cops, or worse. After a while, I told Daddy that I
knew how to do it, and explained my plan to him. We also decided that I
should remain a “virgin” until our ‘wedding night'”

Sundays at our house are quiet and peaceful. My sister is usually at a
friend’s house, and Mom has the day to sort of relax. Now, my mom is a
very easy person to talk to if you have a problem, and I counted on this
to get me through the next day or so. I had packed a bag of some things
when I left Daddy Tom’s place on Saturday evening, and left it in the
trunk of my car until I could retrieve it privately. Mom was sitting in
the living room, reading the paper, when I called down to her, “Mom, are
you busy? “No Honey,” she called back, “What do you need?” “I have
something very important to discuss with you, and need to have a serious
talk. Do you have time, now?” She sounded concerned when she called
back up to me to come on down, she would be in the kitchen. What is it
about kitchens that make them the default place to talk? Anyway, with
shaking knees, I went downstairs and into the kitchen.

I had prepared for this by bringing some clothing home with me, and was
now wearing a semi-sheer white satin blouse, with ruffled bodice, sheer
sleeves, and satin cuffs. Through the material, you could clearly see
my white satin training bra. Below that was a gray wool skirt, white
thigh-high stockings, and my slightly too tight white heels. I had my
hair brushed out, and was wearing some pink lip gloss that I borrowed
from Daddy’s daughter’s room. I was as scared as I have ever been. I
walked into the kitchen, and Mom was sitting in her usual seat with her
back to the hallway. She half turned when she heard the sound of my
heels, and when she actually saw me, she stood straight up, and held
both hands over her mouth nd sort of squeaked. I just stood there, not
knowing what to do next. She finally took her hands away from her face,
and with a quiet voice, asked me why I was wearing such pretty clothes.
Not, “Why are you dressed like a girl?” Not, “What in the hell are you
doing?” No hysterics, just a calm question. I ran over to her as well
as I could in those heels, and wrapped my arms around her, telling her
that I loved her. She told me that, no matter what, she loved me too,
and please, sit down and tell her what the heck is going on.

I told her all about Coach Norton, well, not all about him. I mean, she
didn’t need to know about the bondage, the butt plugs, and the rest. I
told her that I was gay, and that I was in love with him, and all about
the possible move to California, and then finally showed her the ¾ carat
ring on my finger. This was the longest conversation I have ever had
with my mother. We sat down in the kitchen around two in the afternoon,
and only when my little sister called about seven thirty that evening to
tell Mom she was coming home, did I go upstairs, and put my boy clothes
back on. I don’t think that Mom was “cool with the idea,” although I
think she understood that it was something I was going to do, with or
without her approval. She finally gave in, and told me to invite Coach
Norton over for dinner on Friday night, and she would make sure that my
12 year old sister was somewhere else for the night, so we could all

Friday, it seemed, would never come. My mother surprised me on Thursday
night though, by asking me what I was going to wear for dinner. I was
confused, but she continued, “I know that little outfit you wore on
Sunday is the only bit of female clothing you have, and I have to tell
you, it is too, shall we say, revealing for dinner. Now, go get in the
car, and we’ll head up to the mall in Raleigh, to find you a proper
dress and shoes for tomorrow night.” To say I was stunned would have
been an understatement! At my Mom’s urging, I ran upstairs, and put on
my white panties and the bra, along with a pair of jeans, a shirt, and a
sweater. Mom also asked me to bring down the heels that I had worn on
Sunday. She looked them over, and asked me if they hurt to walk in. I
told her the heels were fine, they were just a bit too tight. She
looked at the size, and told me that I was getting new shoes, too.
Three hours later, we walked out of Macys with a royal blue dress, black
stockings, matching black panties and a 34 A bra, a black slip, (Mom
told the lady that the dress was a surprise gift for my sister, and
since we were twins, if it fit me, it would fit my sister!), and
gorgeous pair of navy blue sandals with a 3 inch heel. Mom looked at
me, and asked me if I was really, really serious about this. I just
looked at her, confused again, and told her that, yes, I was very
serious. With that, we took the dress, shoes, and lingerie out to the
car, and she walked me right back into the mall. Mom made a bee line
for a chain hair styling salon, and told the lady that I wanted to have
my hair cut and styled in a very feminine style, but one that could be
brushed out after the “costume party” on Friday. While I was having my
hair washed, cut, and fussed with, Mom said she would be right back. I
guess it was about 45 minutes later that she returned, with some more
shopping bags. My hair was done, and I thought it was very cute, and so
did my Mom. I now had bangs, and my blonde hair was now about collar
length, with a flip to the bottom. The lady had put in some highlights,
and it looked as pretty as any girl at school. Mom paid the lady, and
added a tip, then drug me down the mall to the bathrooms. We went into
the “family” room, where a mother could take a young boy, or a father a
young girl. Mom told me to get undressed, down to my lingerie. She
then handed me a pink T-shirt, a denim skirt, and a pair of pink tennis
shoes. She told me that my jacket was one that either a boy or girl
might wear. Once I was dressed, and also completely embarrassed by
having my Mom see me in panties and a bra, we went back out into the
mall, where we stopped in an accessories shop, and had my ears pierced,
and a small pair of gold studs installed, and then it was on the nail
salon, where I had a set of not too long nails applied, and painted a
pale pink color. You could have knocked me over with a feather! Mom
told me that if this all meant that much to me, then we had better do it
properly! Mom came to the mall with a son, and left with what looked
like a daughter, and I don’t think I have ever been happier! So much
had taken place so quickly, that I felt like I was in a blissful dream,
and was afraid that at any moment, I would wake up.

I stayed home from school on Friday, as the earrings, hair, and nails
would have been very hard to explain. Mom strayed home from work, too,
and spent the time teaching me how to walk in heels like a lady, how to
sit, stand, and get in and out of a car, without showing my panties to
the world. Finally, I got work cleaning the house, while Mom got dinner
ready. She had started her homemade spaghetti sauce early that morning,
and the house was full of the aroma. At six, my Mom shooed me up the
stairs to get a bath. She told me to call her when I was dry and had my
new panties on. I did, and she used body talc on me, helped me to put
on and adjust my new bra, put on my stockings and finally zipped up my
new dress. she sat me down and brushed my hair, and applied a little
eye shadow, and some pale pink lipstick that matched my nails, and
pronounced me ready. I stood up, and looked in the mirror, and saw
nothing but a 12 or 13 year old girl dressed for a party! I twirled and
turned in front of the mirror until my mother burst out laughing.
“Well, if I had any doubts before, they’re gone now!” she chuckled.
“You preen in front of that mirror like a proper girl!”

When the doorbell rang just a few minutes after seven, I answered it,
and there stood Tom, or Daddy, or Coach, wearing a pair of gray wool
slacks, black loafers, a black turtleneck sweater, and a gray tweed
jacket. He looked beautiful! He took me by the arms, and held me, just
running his eyes up and down, and finally kissed me gently on the lips.
I won’t bore you with the dinner and the conversation that went on until
well after midnight. Suffice it to say it covered a lot of ground, from
legal issues, to morals, to finance, to social concerns, and more.
Around ten, the conversation turned to a more practical matter, our
wedding. Mom and Tom (We had decided to dispense with “Daddy” in front
of my mother) eventually agreed that we would rent a small wedding
chapel in Raleigh, and that a friend of Tom’s would serve as the
presider. We decided to use the Methodist service, but leave out a lot
of the religious aspects, and wherever the word lawful or legal was
there, replace it with the word loving. At the door, Tom took me in his
arms and kissed me like there was no tomorrow, right in front of my
mother! What could I do, but wrap my arms around him, and kiss him
right back! It was going to be a long winter, waiting for the school
year to end, and my beautiful June wedding day.

Christmas came, and both my Mom and Tom bought me lots of beautiful
clothes. By now, my younger sister, Stephanie knew, and she promised to
keep it a secret. Tom and I did not see each other as much as we wanted
to, as my mother wanted us to keep a low profile. I did wear a girl’s
nightie to sleep in every night, and Tom brought over my pink robe and
slippers, but that was about the extent of my girly dressing. Mom spent
the time teaching me to wash, iron, cook, and clean for my new husband,
and often had me working in high heels to get used to them, as Tom had
told her I was not going to be allowed to wear other types of shoes.
When I went to Daddy’s house, I always wore the most beautiful lingerie,
and nightgowns, and when we went to dinner (way out of town) I always
wore at least panties and stockings under my slacks. The only other
dressing that was done in our home was trying on all the pretty things I
got for Christmas from Daddy, and even some lingerie from Mom, and a
beautiful ivory colored, baby doll nightie and perfume from my little
sister! Mom kept all of “Michelle’s” things in the spare room closet,
ironed and in plastic bags, ready for my honeymoon and new life. The
winter dragged on and on, and finally, it was spring and school was
over, and the day was right around the corner. Mom and I had bought my
wedding gown on-line, and one of her good friends did the fitting as a
quiet favor. It was a dazzling white silk dress, off the shoulders with
¾ length sleeves, and a full skirt with layers of crinolines, all
dripping with lace and a few well placed seed pearls. I decided that I
would wear a traditional veil, and carry a bouquet of pink roses
arranged with baby’s breath.

The day dawned clear and warm, with none of the humidity that eastern
North Carolina is known for. We made it to the chapel in plenty of time
to get dressed, in spite of traffic and a fender bender blocking the
road. My sister was my maid of honor, and wore the most gorgeous pale
green taffeta dress, that really set off her hair and eyes. Mom wore a
very nice dress of ivory silk with a muted pattern of climbing roses,
and she never looked more beautiful. Under my dress, I wore my white
satin corset with the baby blue lace overlay, as something old and
something blue, white satin panties with ruffles and a ribbon at the
back that laced up the middle, and kind of hugged my butt crack. Thigh
high stockings with a lace pattern adorned my legs, and under my dress I
wore some things that Daddy insisted on. Six inch stiletto heeled pumps
meant that I could not walk, only mince, and a tight, knee length hobble
skirt that ensured that I “couldn’t run away!” To complete the “wedding
party,” one of Tom’s good friends stood up as his best man, and wore a
bow tie that matched my sister’s dress. It was all so perfect, that I
wanted to start bawling before the ceremony even started!

I don’t remember the details of the wedding at all. I do remember Tom
slipping the ring on my finger, and then lifting my veil for a kiss.
And, I don’t think any couple, no matter what the gender, ever kissed
with that much love and passion. It was a time of pure magic. We had
our pictures taken by another friend with a good digital camera outfit,
suffered through a very short reception, and we were finally alone. I
do remember one detail from the reception that really got a few laughs.
My sister, Stephanie, after everyone else had made the required toasts,
stood up, told us that she hoped we would be very happy, and then
announced, “When I get married, I want to wear the same dress my brother
is wearing, and I hope I look as beautiful in it as he does!” Tom had
hired a white limousine, and the driver was so sweet as he helped me get
my skirts into the car without getting them dirty! On the short drive
to the hotel, we could not stop kissing, and I’m sure the driver was
watching. Boy would he have been surprised to learn that both the bride
and the groom were sporting hard-ons!

We swept up to the reception desk. Tom looked so suave and masculine in
his black tuxedo, and on his arm, a blushing bride in full regalia, just
basking in his manliness. I know my legs got looked at as I held up my
dress to walk a bit easier. Of course, the very tall silver heels
attracted attention, and the fact that I had to take little, tiny steps
allowed everyone to get a good look! Again, what would they all have
thought if they knew what was under the bride’s satin panties? Into the
elevator, into the hall, and there it was, the door to the Bridal Suite!
This was too perfect, too storybook to be real! The bellhop unlocked
the door, Tom gave him a tip, and then without any warning, picked me
up as easily as if I were a baby, and then we were behind closed doors,
as man and wife, or at least as man and sissy wife.

Daddy told me to go into the bathroom, and remove only the hobble skirt,
go to the “potty” if I needed to, and come back out. I complied, and
came back out to a bottle of champagne on ice, and my darling husband
standing there, his jacket and vest off, bow tie undone and hanging
loose in his collar, and looking so handsome! I felt like the luckiest
girl, or I mean luckiest boy, I mean, well, I was so lucky! He swept me
into a passionate embrace, holding me tight to him as he kissed me,
hard. He then began kissing my cheeks, my forehead, lightly brushing my
eyelids with his kisses, and I in turn, just melted on the spot. He
broke away to pour us each a glass of champagne, and we toasted each
other. He handed me his empty flute, picked up the cooler, and motioned
me to precede him into the bedroom. There, he once again wrapped me in
his arms, kissing me and caressing me. Finally, his hand went to my
back and slowly lowered the zipper of my gown. It swished to floor, and
then the crinolines followed, and I stood before my new husband in
corset, panties, hose and heels. Without a word, I began to undue to
studs on his shirt and cuffs, removed the shirt, and then dropped to my
knees amidst the folds of my wedding gown, and slowly unbuckled his
belt, undid the catch, lowered the zipper, and then all that was between
me and his wonderful cock was a pair of black silk boxers. I kissed
and nibbled his thick hard member though the material, and finally
released his monster into my waiting, pink painted lips. I never wanted
anything as badly in my life, as I wanted that cock in my mouth! I
kissed and licked him, sucking the head into my mouth, and swirling my
tongue around it, feeling the heat, and the soft, velvet hardness of it,
and then took it deep into my throat, relishing the feel of it filling
my mouth. I wanted him to cum in my mouth, to taste his salty man
juice, but after a few moments, he pulled out, and lifted me to my feet.
“Missy, my dear bride, it’s time I ended your virginity and made you my
wife! I wanted that too, but I was scared. I knew that the plug I
had been practicing with, and often wearing for hours at a time, was
less than half as thick as Daddy’s cock, and not nearly as long. I was
sure I would be split in two by him! I had a realistic rubber dildo
that I used to practice sucking, and to “deep throat” without gagging,
but I was forbidden to use it on my bottom, or anything bigger than the
plug that Daddy gave me. It was “crunch time”.

“Missy,” he spoke again, breaking my thoughts, “I know you want your
first time to be special, but so do I. You know that in all things, you
are my slave, my servant, and my submissive. You’re first time will be
in bondage, because that’s the way it has to be.” I nodded, having
already figured out that little detail. He led me to the bed, and told
me to turn around, and open my mouth. He stood behind me, and inserted
the penis gag into my mouth, buckling it tightly behind my head, then
lowering the veil I still wore down over my face. I was placed in my
satin mittens, and they were buckled onto my wrists. He told me to put
my arms behind my back, and then I heard him rummaging around in a
suitcase. He then placed a leather sleeve over both wrists, and I felt
him lace the sleeve loosely over both arms. I grunted in real pain as
he pulled the laces tight, forcing my arms together behind my back, my
elbows almost touching each other. my ruffled white leather collar was
then locked around my neck. My Daddy then added a new wrinkle. He
produced beautiful little silver clips, and proceeded to place one on
each nipple, causing me to gasp in pain. I was told to get onto the
bed, and kneel, which he helped me to do. The cuffs were placed back on
my ankles, and the spreader bar once again held my legs spread. He
placed two pillows under me, covering them with a towel, and told me to
lay down over them. The final touch was a strap that he hooked to my
collar, and then ran back behind my knees, and back up to the collar,
pulling it tight, forcing me into an even tighter crouch, pushing my
poor bottom skywards. I could not move an inch in any direction, could
not move my hands, or even use my fingers, and calling for help was
right out of the question. My nipples were on fire from the clamps, and
my shoulders and arms ached already. Slowly, he caressed my pantied
bottom, and then pulled on the little satin ribbon that laced the two
halves of the panties together, exposing my virgin asshole, without
taking off my girly panties. With exquisite slowness, he fingered, and
then licked my rosebud, sticking his tongue between my cheeks, almost
causing me to cum right then and there. After a long, sweet time, I
felt him stick his finger up my bottom, and could feel the cool lube
being applied. He then did a curious thing, and stepped away from the
bed. I heard him fumbling with something, and then was blinded by the
flash of a digital camera, recording my bondage and vulnerability.
Daddy took at least 10 pictures before he put the camera down, and once
again, stood behind me. With soothing words, he placed the head of his
cock against my virginity, and without any warning, rammed it into my
bottom. I screamed and screamed into the gag, trying desperately to
wiggle free of this horrid thing. I knew there had to be gallons of
blood pouring out of me, as he ripped me in two! He just stood behind
me, not moving at all, his hands rubbing my shoulders and my ass,
reaching around to touch my still hard cock, and then to tweak my
burning nipples. The pain began to subside, and with it, my attempts at
freedom, and he began to rhythmically fuck my bottom, sliding his huge
cock almost out, and then ramming it home again. I could feel his balls
slap me as he came forward. Faster and harder he fucked me, and I found
I was attempting to meet his thrusts by pushing back with my ass,
although I had only millimeters of movement allowed me by the bondage.
The pain in my nipples and arms, blended with the wonderful feeling of
that cock sawing into me, and I suddenly realized the connection between
pleasure and pain, and relaxed into the experience. I felt Daddy tense
up, his cock swelling even more, and then he filled my bottom with his
wonderful seed. At almost the same time, I filled my panties with my
own cum, and I knew that I was now Daddy’s wife, his slave, his personal
slut, and wanted nothing else in this world than to continue.

I could feel his cock soften, and finally, he pulled out of my bottom,
leaving me feeling very empty. He kissed me on each cheek of my ass,
and then, leaving me hog ties and gagged, went into the bathroom to
clean up a bit. A minute or two later he came back to the bed, and
began to let me out of my restraints. First he released the strap to my
collar, and helped me back to a kneeling position on the bed. Next, he
removed the arm binder, and massaged my shoulders and arms until the
circulation started back. The ankle cuffs came next, and he helped me
to stand on my feet, and held me until my rubbery legs came back to
life. He told me to stand very still, and to relax, and released my
nipple clamps, which hurt worse than putting them on, causing me to
scream into my gag yet again. With infinite kindness, he gently kissed
and licked each nipple until the fiery pain subsided. At last he
removed my veil and took that huge rubber penis out of my mouth, and I
wrapped my mittened hands around his neck, kissed him, and told him how
much I loved him. He led me to the bathroom, and for the first time, I
noticed a huge whirlpool/Jacuzzi tub, that was already filling with hot
water. While it finished filling, Daddy lovingly undressed me, removed
my mittens, and helped me into the tub. He got in, sitting behind me,
and turned on the bubbles, massaging and rubbing my aching body, all the
time telling me how much he loved me. The only jarring note for me was
that in the tub, devoid of my feminine trappings of satin and lace, I
was just a boy. I wasn’t special any more, at least to my eyes. Sure
my finger and toenails were painted pink, and my hair was done in a very
feminine flip, but to mind, something was missing. My symbols of being
a sissy were strewn on the floor between the bedroom and the bathroom.
He told me not to worry, that he still thought of me as his sissy slut
wife, and that made me feel much better.

Once we finally got out of the cooling tub, he helped me to dry off, and
then presented me with a white satin teddy, with ruffles around the leg
openings, and panels of lace and pretty white bows. There was a
matching sheer bed jacket, and at his urging, I put on a pair of white
thigh high stockings that had rubber around the inside of the tops to
hold them up, and put my silver wedding shoes back on. I fixed my hair,
redid my lipstick and eye shadow, and sat down while Daddy called room
service for dinner. While we were waiting, we cuddled and kissed, and
finished the champagne. A very short time later, there was a knock on
the door, and I jumped up to hide in the bedroom, but Daddy put a hand
on my shoulder, and told me to sit right there. When the waiter came
in, he had no trouble identifying me as a boy dressed in lingerie, and
living with a man in the bridal suite. I was so embarrassed, I could
feel my cheeks heating up, and could only stare at the floor. Right in
front of the waiter, while he was setting up the dinner, Daddy told me
to go into the bedroom, and hang up my wedding gown, which I think
caused me to blush all the way to my knees! I could feel the waiters
eyes following me out of the room, and then heard Daddy chuckle and say,
“She does have a cute little ass and nice legs for a sissy boy, doesn’t
she?” I dashed as fast as I could for the safety of the bedroom and
closed the door, and just started to cry. I felt so violated and
exploited. Why did he do that to me? I already knew he owned me, I was
his! Why this display of macho power when he just had me, trussed up,
powerless, and willing? I just stood up in a wedding gown, and publicly
professed my love for this man, and now this? I was hurt, and angry,
and sad. Daddy knocked on the door, and quietly came in. “That upset
you, didn’t it my precious?” He asked quietly. I just nodded.
“Remember, Sweetheart, you are now my property, and even though I love
you, and want you with me always, you have to understand your place.
That was just a small lesson for the rest of our lives. Remember this
lesson, and you’ll do just fine. Forget, and you will be sorry. That
overpaid busboy is a nobody. Sure he’ll gossip, and within the hour,
everyone who works here will know that you are a gay sissy, and that I
married a sissy. But who cares? We will be here for a few days, and
then it’s on to our honeymoon, and on to our new lives together, twenty
five hundred miles from here. Now come and eat, my love.” I dried my
eyes, went back to the bathroom to fix my makeup again, and joined my
husband for a dinner of lobster tails, shrimp, oysters, and more

Over the next few days, we sucked and fucked like minks. Sometimes I
was bound, others, I was just dressed in a nightie, and free to explore
my Daddy’s body, and he to explore mine. It was three days of bliss,
marred only by a few other public displays of his new sissy bride. The
first was the next morning, when he had me dress as a fantasy French
maid, complete with locked-on high heels, and my gag. My outfit
consisted of a black satin dress with a white satin pinafore style apron
tied in a big bow in back. The dress itself was way too short, held out
from my body by multiple layers of crinolines which showed off my black
satin panties with white lace trim. You could also see my garters and
black seamed stockings. I also wore the mandatory white ruffle of lace
around my throat, and white lace cap. The finishing touch were the
black pumps with 6 inch heels, and short silver hobble chain that went
from shoe to shoe to make sure I took little “lady-like” steps. When
the maid came in for room service, Daddy told her that he had a sissy
boy maid who was going to help her, and that she was to tell me what to
do. The maid was a chunky Hispanic lady, who thought the whole thing
was a hoot (She had heard about the sissy in 614, and now she knew it
was true!). She had me clean the toilet and dust, all the while bending
from the waist, and not the knees, so my pantied ass was on display.
She also made me go out at least three times into the hall to get
something off the maid’s cart that she “forgot.” Then, as she made me
vacuum the suite, she kept swatting me on the ass, and telling me that I
had missed a spot. I was totally, thoroughly, and completely
humiliated. She even asked Daddy if I still had my “boy parts, and he
made me stand there, and lower my panties so she could see my shaved
cock and balls. What surprised me was that as humiliated as I was, I
was as hard as a rock! The maid left, laughing at the sissy in the
maid’s dress, and Daddy was so turned on that he pushed me over the back
of the chair and with just a little spit for lube, took me right there
in the living room. When he was done, he spun me around, knelt down in
front of me, and gave me the best blowjob I have ever had. There was
something to this whole humiliation thing!

My final piece of humiliation for the weekend came the morning we were
packing to leave. He reached into a dark plastic clothing bag that was
hanging in the closet, and pulled out my pink satin sissy baby dress.
It was back into that thick cloth diaper and pink plastic panties,
covered with those beautiful satin sissy panties. I was dressed, and
locked into the dress, and he handed me a little baby doll to hold. He
placed a large NUK pacifier in my mouth, tied it behind my head, put on
my bondage mittens, my pink satin bonnet, sissy anklets and black Mary
Janes. The final indignation was when he produced a harness and leash
made of pink leather, just like you might use for a toddler in a mall,
put it on me, and then called downstairs for the luggage to be picked
up. It was at that moment that my mother and my little sister came to
the suite to pick up my dress to be cleaned and stored. They obviously
thought we had already left. I found out later from Daddy that he
planned on my mother seeing me this way, to make sure that everyone
“knew the score.” She just looked at me, looked at Daddy, kissed me on
the cheek, and wished me luck. I’m sure she was shocked, and curious,
but kept her questions to herself, at least for the time being.
Stephanie, on the other hand, walked all around me, touching the dress,
lifting the hem to see my panties and diapers, giggling loudly. She
even stuck her hand down the front of my plastic panties to see if “baby
was wet!” I felt very low right then. The bellboys got there and
picked up the luggage laughing at me in my dress, and Daddy walked out
with them. I started to follow, but he told me to wait. I stood there
in the open doorway for a moment, and then a woman got out of the
elevator, and walked up to Daddy. He handed her some money, and she
walked up to me and without a word, took the leash, and led me to the
elevator. She was tall, with long brunette hair, and very pretty. She
was dressed in a white blouse, and a gray jacket and skirt that looked
like a business suit, but with a short skirt and very high heels. I
wondered if she was a business woman, or a friend of Daddy’s, or what.
Turns out, she was a business woman, if you count the escort business!
She led me off the elevator, and into the lobby. It was Monday, and the
place was busy with businessmen and women, and the whole place just
stopped, stared, and then began laughing as one. As if the over-the-top
sissy dress, oversized pacifier, bonnet, mittens, and sissy panties on
display weren’t enough to incite laughter, the back of the harness had
the words SISSY BABY BOY written in rhinestones! I froze in the middle
of the lobby, and without a word, the lady sat down on the edge of a
stone planter, and pulled me across her shapely legs, and proceeded to
spank my diapered butt. It didn’t hurt, but it was so embarrassing!
With each smack, she yelled, “I (whap!) told (whap!) you (whap!) that
(whap!) I (whap!) would (whap!) not (whap!) put up (whap!) with (whap!)
your (whap!) silly (whap!) sissy (whap!) nonsense!” She stood me up and
I was crying from the sheer humiliation of it all, but she continued in
loud voice, “I just can’t believe a boy like you wants to dress up like
a baby girl anyway. Now look at yourself, crying like a baby, and I’ll
bet you even wet your diaper like a baby. You disgust me!” With that,
she jerked the leash, and walked me to the waiting limo, my head hanging
down, and my cheeks hot with shame. But, in spite of myself, I could
feel my cock trying to tear its way out of its cotton, plastic, and
satin prison.

Daddy was waiting in the limo, and it took us to the private side of the
airport, and pulled up next to a sleek white private jet that Daddy had
chartered, and my further exposure to the world was mercifully short.
Once on the plane, I was allowed to remove my dress, but sat there in my
diaper, bonnet, and mittens. After a while, Daddy unbuckled his belt,
and we sat together on a leather couch, and cuddled and kissed, Daddy
finally forcing me to my knees and, while I might say I gave him a blow
job, the truth is that he rather forcefully fucked my mouth. He then
told me to get up, and go the bathroom. There, he told me to sit on the
toilet seat, and open my mouth. He then admonished me to not spill a
drop, stuck his cock back in my mouth and began to pee! I was shocked,
but he would pee, cut off the flow, and I would swallow, then he would
do it again, until he was dry. It tasted horrible, and I never wanted to
do it again, but he told me I was being punished for not walking across
the lobby like a good little girl, and for making a scene. I was mad,
and wanted to tell him that the “scene” was engineered, and not of my
own doing, but I realized that it was all part of his plan, and that I
would have been “punished” anyway. Daddy wanted to, Daddy liked it, so
Missy took it. He finally took off my baby things, and I was allowed to
brush my teeth. Then I got dressed in a pretty peach silk dress, with
white high heeled sandals, and what Daddy called my “outside bra.”
Instead of a training bra that did nothing but emphasize my flat chest,
this bra had inserts that gave me a B cup bosom, and did a lot to hide
the fact that I was a boy, not a girl. Daddy told me that the vitamins
that my mother had been giving me were actually a low dose hormone, and
that with some special cream that I was to start using, I would develop
little titties of my own. Not too big, Daddy warned, because I was
still his sissy, and he wanted a sissy slut for his wife. The rest of
the way to San Francisco, we discussed what we would do and see, where
we move to after the honeymoon, and all the things a newlywed couple
would discuss. I knew that I had some lessons to learn, and would have
to come to terms with my new status, but I also knew I was loved, and
needed, and wanted my Daddy’s cock up my boy pussy and in my mouth for
the rest of my life.

3 Responses to “A Very Sissy Love Story”

  1. leslie michaels Says:

    i’m a sissy boi although much older who whould be so happy to be as lucky as missy is in this story it was truly a wonderful story

  2. Roland Says:

    I would like to be a sissy boy like that too , love to wear pantys, look for equal thinking boys an men romuell22@yahoo.de

  3. Anonymous Says:

    Wow! Well written and just hands down the sexiest thing I’ve read in quite some time. Woofty!

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