Date: Tue, 10 Jan 2017 21:50:15 +0000 (UTC)
From: Robin Buckman <pink_pantyboy@yahoo.com>
Subject: 'Bitchboy' - Domination - Force fem - bondage

(Boy to sissy bitch - conversion )

Bitch Boy

By

Pink Pantyboy

"You wanted to see me, sir?"

"Come in, Jack and close the door please." Jack came in and closed the door
behind him, looking a little nervous, and so he should be having been
called to come into the boss's office just before he was about to go home
for the day.

"Take a seat, as we need to have a talk."

"Yes, sir." He sat, nervously rubbing his damp hands on his pant legs.

"You've only been with us for three months, Jack, and I thought of making
your temp position permanent."

"Yes, sir." He looked up at me expectantly. With nothing but short term
temp work and sitting around waiting in between jobs was stressful and hard
of the pocket book.

"One thing I told you about when you started was about tardiness, and in
the last three months you have been late eight times."

"Yes, sir, but some morning the traffic is very bad..." I held up my hand
to silence him.

"I'm not interested in excuses, Jack. Knowing the traffic is going to be
bad, you should leave for work earlier."

"Y...yes sir." He murmured, looking down. I looked at his employment
application on the screen, seeing he lived less than five miles from the
office. At eighteen and just out of high school this was probably his first
full time job, and from the address his apartment was in a less that
desirable neighborhood, but the rent was cheap.

As the office gofer, it didn't pay that well and between his rent, the
running cost for his junker of a car, insurance, food, gas and electricity
he probably didn't have much left over. Getting fire from this job would
put him in a real bind if he couldn't get another job right away. This gave
me a certain amount of leverage over him and I meant to take advantage of
that if possible. It all depended on how desperate and pliant he was. One
thing I'd noticed was how meek and susceptible to intimidation, backing
down when the more aggressive guys in the office picked on him. I'd already
fired two on them so he looked to me to protect him to a certain extent,
which I did. I used this to make him work late, run out for food or coffee
when I needed it or any other make work job I couldn't think up. Jack was a
rather effeminate young man, slim, medium build with small hands and feet
and overly long, light brown hair that almost came down to his shoulders.
Not that it was unusual nowadays, as a lot of young men wore their hair
long. Jack's was rather unkempt, as if he hadn't taken the time to comb or
brush it before coming to work.

"I'm trying to decide what I should do with you, Jack, fire you for this
continued lateness, or some other form of punishment." He jumped when I
said punishment rather than when I said fired.

"Please... I'll do better I promise... it's... it's just the traffic.
Please don't fire me." He pleaded in a soft voice."

"Jack, you only live five miles from the office, so please don't use
traffic as your excuse for coming in late. Staying up playing video games
or watching porn would be my guess. Which is it?"

"What... no... I don't..."

"Not that it matters. My son use to stay up late doing both, but putting
him over my lap and giving him a bare bottom spanking a few times cured him
of that nasty habit." Jack's face turned bright red and dropped his eyes
hearing that.

"Yes, sir."

"I suspect your father had to do that a few time to you, right?" Jack
nodded. "Thought so, but seeing as I'm not your father and can't spank you
like you should be, my only alternative is to let you go." I almost held my
breath wondering which way he would jump. I sat silent and let the image of
him getting an over the knee, bare bottom spanking percolate through his
brain until he came to the inevitable conclusion that is was a spanking or
getting let go. The prospect of not being able to pay the rent or put gas
in his car to get to work if he found another job reached its logical end.

"Please sir, I'll do anything you want, but please don't fire me... I won't
be able to make the rent or pay for me car this week if you do." He almost
sobbed.

"The labor relations act prevents me from applying and other forms of
punishment, Jack, and as I said, not being your father nor having the right
to punish or spank you, I have little alternative but to let you go." He
looked up at me and took a shuddering breath, his face turning red.

"Y... you could spank me, sir." He murmured very softly.

"What did you say?" I needed him to say it out loud, feeling myself harden.

"Y... you could spank me for being late instead of letting me go, sir." He
said a little louder.

"You know what you're asking me to do, Jack? It's against the law and I
could get into real trouble if you told anyone." He nodded. I sat there,
swinging my chair back and forth as if in deep thought, which I wasn't.
Inwardly I was smiling, having guessed right about him. Now to play it
right and put it all on him.

"Tell you what. Go and lock up and think about it. If you change your mind,
put the latch on the door and just leave. I'll put it down that you just
quit and leave it at that."

"Y...yes, sir."

"If, and I say, if you come back, I will spank you instead of firing you,
but it will be a proper spanking, Jack, the same as I'd give my son if he
was in the same position as you. Pants down, over my lap, clear?" He nodded
and stood, almost running to the office door. I half expected him to change
his mind and just leave, listening to him walk to the front door, then
smiling as I heard his footsteps coming back. He did take his time, and
stood in my office doorways for a moment as if thinking about what was
going to happen.

"Come in and close the door, Jack." I said, standing and closing the window
blinds.

The office was on the third, and top floor of the building so there was
little chance of anyone seeing what was going on, but why take the chance
of someone in a nearby office building seeing in. Besides that, I wanted a
feeling of intimacy so I switch off the overhead light and just left my
desk and wall lamps on, giving the office a warm soft secretive feeling.
Before standing, I adjusted my hard cock into a more comfortable position
so it wasn't as obvious, and then walked over to my couch and sat down,
motioning him over.

"Come here, Jack." He slowly shuffled over and I pulled him round to my
right side, feeling his shiver as I did. "Undo you pants." I ordered,
making my voice a little sterner.

"Please..."

"I told you how it was going to be, Jack, so undo your pants!" With a
little sob, he unbuckled his belt and pulled the zip down.

"Tell me why you are getting this spanking, Jack?"

"F... for being late to work... sir."

"So, this is your fault, isn't it?" He nodded. "No, I want to hear you say
why you are getting the spanking out loud." He sobbed again and sucking in
a deep breath. Making him admit what he'd done out loud to get the spanking
would deepen his feeling of shame and humiliation.

"For being late..."

"No, I want you to tell me exactly what you did and what is going to
happen." He let out a louder sob.

"I'm getting a spanking for being late to work, sir." He sobbed.

"Good, I'm glad you understand that this is all your fault and only getting
the spanking you deserve." Saying that I reached over and pulled his pants
down. He grabbed the belt and tried to hold them up for a second, but I
pulled them down his knees against his weak resistance and exposed his
white boxer shorts.

"Now get down over my lap!" He didn't move so I grabbed his arm and pulled
him down.

"Oh god!... please." He sobbed and I pulled him over my lap into the right
position. Anticipating he would start kicking, I put one leg over his to
hold them down.

"Keep your hand in front of you. If you put them back, I'll spank you twice
as long and twice as hard, understand?"

"Please..."

"Understand?"

"Y... yes, sir." I then hooked my thumbs into the waistband of his
underpants and slowly worked them down over his bottom. I did it
deliberately, rather than just jerk them down, as I wanted him to feel as
ashamed and humiliated as possible. I knew from experience he'd remember
that feeling, and his underpants being pulled down for the first time. I
worked them down to his knees so his lily-white bottom and upper thighs was
exposed to my hand.

"Oh god, please... no." he sobbed as I ran my hand over his bottom, feeling
his quiver and shake.

This was nothing like the spanking his father had given him. That was just
punishment. This was something else. I doubt he'd felt ashamed and
humiliated when his father spanked him, but I knew he did this time. Now,
he was laid over a strange man's lap with his pants and underpants pulled
down, and about to get spanked like a naught little boy. He didn't know it
yet, but I was going to spank him until he was crying his eyes out and
pleading with me to stop. Gripping him by the back of his neck I started
spanking him then, slow stinging slaps on each check. He jumped a little as
each slap landed and let out a small sob but still tense and trying not to
cry. Once I had his bottom nice and pink I ran my hand over the smooth
hairless skin, feeling him tremble.

"Now you're ready for your spanking, Jack."

"What?"

"As I said, you are going to get the same spanking as my son would get."
Saying that I pulled out the paddle from under the seat cushion and laid it
on his bottom so he could feel it.

"Ohhhh noooo... please.... Not the paddle..." I didn't give him time to
finish what he wanted to say, but started spanking his bottom all over. It
didn't take long before he started squealing and whimpering, begging me to
stop. I kept it up, not hard, but waiting for him to start fighting, which
I knew he would in a moment. It took a little longer than I thought, but
eventually he did, struggling to get his feet under he so he could
stand. With my leg hooked over his, he couldn't of course, but he fought to
get away. Now I started on his upper thighs, hard stinging slaps of the
paddle. Now he squealed out loud, swearing and sobbing, begging me to
stop. I didn't and started spanking his red bottom again. It didn't take
long before he slumped over my lap in defeat and just lay there crying his
eyes out, jumping and squealing each time the paddle landed. I'd won and
he'd submitted to my dominance over him so I only spanked him a few more
time to drive the point home and stopped. Next, I slipped him off my lap
onto the floor between my open legs and he immediately grabbed his burning
bottom, head down sobbing and crying. Without him knowing it, this was a
perfect submissive position and with the proper handling, he'd be there a
lot. Taking a tissue from the box on the table beside the couch, I lifted
his head and wiped his eyes.

"There, there. I know it was hard, but you know you deserved it, didn't
you." He looked up at me with pleading eye and nodded.

"Tell me out loud. You deserved it, didn't you." He let out another sob of
shame.

"Y... yes, sir. I deserved the spanking for being late."

"Here, blow your nose." I said, handing his a bunch of tissues. He did, but
I took more and holding him under the chin I lifted his head and dried his
eyes again.

"I'm surprised at a strong young man like you crying from a little
spanking. My son never cried. He said that only sissy boys cry when they
get spanked." He let out another sob. "I guess that makes you a sissy boy,
doesn't it, Jack." I laughed softy.

"N... no, sir. I'm not a sissy... I'm... I'm a man." He said softly.

"Good. Now dry your eyes and go wash your face. We don't want anyone
outside of the office knowing what a sissy you are, do we." He shook his
head as he stood, reaching down to pull his pants up before going off to
wash his face.

The seed was planted, all that remained was for me to watch it grown. As he
stood, I quickly reached over and deliberately pulled his underpants up,
adding a little extra humiliation as I could see his cock and balls, which
were rather small for a young man of his age, adding to his status of a
sissy boy. All being well, I'd soon have him wearing panties instead of
men's underpants.



* * * * * *

As promised, Jack started arriving at work ten to fifteen minutes early
each day after that and I wondered if my spanking had been too hard. I
expected him to fuck up again and give me a reason to paddle his bottom,
but for two weeks he didn't give me any excuse. That made me wonder what
sort of porn he was looking at, and for that, I needed to take a look
inside his computer. It wasn't hard to get a copy of his door key as I
simply asked him for his keys one day saying that I needed to move his car
as it blocked the dumpster pick up. Usually the only place left for him to
park was next to the dumpster so I moved his car and had a copy of his
front door key made at the hardware store just down the block. I covered my
extended absents by bringing him a orange juice and a coffee for myself and
dropped off his keys along with the juice. After lunch, I gave him the job
of cleaning up the stock room, which was a bit of a mess, so I knew he'd be
busy the rest of the day.

The key copy worked perfectly and I slipped into his dingy apartment
without anyone noticing, and as I suspected the place was a mass, what with
clothes and dirty dishes all over the place. I did search his chest of
draws but didn't find anything unusual until I spotted some colored
underwear at the bottom. Carefully I unearthed them but was a little
disappointed to find they were just unisex underpants, not the panties I
was expecting. They weren't exactly girl's panties, or guy's underpants but
they didn't have a front opening so that put them in the panty department
as far as I was concerned. It was a start so I carefully replaced them, and
the others on top, not wanting him to suspect someone had been riffling
through his underwear. My main concern was his computer in the corner of
his bedroom. The silly fucker hadn't even bothered password protecting it,
and with just a few key strokes, I was in and searching through his web
browser to see what porn sites, he visited. Most were the usual, such as
`Porn hub' with short fuck and suck videos but there were one or two with
guys fucking and sucking other guys. I checked and found one site he
visited a lot but this turn out to be a lingerie site with girls modeling
various types of slutty underwear. Looking at the time, I realized I didn't
have time to search his computer properly, so I loaded in the key logging
and remote entry program on to his systems. This would give me access and
control of his computer and permit me to search at my leisure to see and
watch what porn sites he visited from my office or home computer without
him knowing it. I even disabled the ready light on his cam so he wouldn't
know if I was watching him. His refrigerator offered up a selection of soft
drinks, mostly orange juice, and lemonade, so it was easy to inject a
little chemical cocktail into each, and the mike carton. If things went
well, he'd soon start showing the results of the estrogen and
beta-blockers. Returning everything back to where it was when I went in I
carefully checked that nothing was out of place and slipped back out of his
apartment without anyone seeing me.

Of course, I gave the stock room a look of disapproval at how he'd cleaned
it up, grumbling something inaudible about sloppy work and left him to
it. A sheet metal screw under his rear tire made him late for work the next
day as the slow leak took several hours so by the morning the tire was
flat. I made a show of standing in the doorway to my office and pointedly
looking at my watch as he rushed in. Jack went red and quickly went to his
desk, his dream of slipping in unseen evaporating like the morning
mist. However, I didn't say anything, wanting a more serious excuse before
I called him on the mat. It came the next week when he jammed up the copy
machine and I had to bring in the tech to fix it, little knowing I'd fixed
it so it would jam. One look at my face and Jack knew he was in trouble
when he saw the cost of the technician's time but again I let his sit and
stew. During this time, I'd searching his computer and copied the names,
addresses, telephone number and email addresses of all his friends and
family, knowing it would come in handy a little later. I also watching him
browse the web and found it instructive, especially the chat room he when
to. Much to my delight, this was a sissyboy chat room and he liked the
dirty perverts on there to talk nasty to him. He was particularly attracted
to man that verbally humiliated him and called him nasty, filthy names,
betting he was jacking himself off while they did. That was good, as I now
knew what turned him on. A couple of time he admitted he was wearing girl's
panties and knew he was wearing one of the ones I'd found in his
draw. Another of his favorite site was a porn site that had a lot of
spanking videos on it, both girls and boys getting spanked and some getting
fucked, or giving blow jobs, some dressed, some naked, even some with boys
wearing frilly panties getting their tight round bottom spanked by men and
women.

"Come in and close the door, Jack." I said, motioning him in. "Did you lock
up?"

"Y... yes, sir." He murmured as I lowered the blinds. One look at his face
and he knew what that meant, seeing his lower lip and chin start to quiver.

"Please sir. It wasn't my fault... my tire got a puncture and I had to
drive to the auto shop to get it repaired."

"Why didn't you use the spare?"

"The spare was flat as well."

"Laziness is no excuse, Jack. If you'd fixed the spare you wouldn't have
been late, would you?" Putting it back on him.

"N... no sir."

"I told you before, Jack. I'm not interested in excuses, and a flat tire is
a poor excuse for staying up late and watching porn and playing with
yourself." His face turned bright red and a tear ran down his cheek. I
pointedly took the paddle out of my desk draw and placed it on the desk.

"Just like last time, Jack, your choice."

"P... please, not the paddle... it hurts." He whined, letting out a sob.

"One or the other, Jack." He knew exactly what I meant. He hesitated and
then turned and closed the door.  Walking over, I stood by the couch again
and motioned him over. Dragging his feet, he walked over to stand in front
of me, looking down at the floor. I lifted his chin so I could see the
tears running down his face, sighing as I did.

"You are such a little sissy, crying before I've even started spanking
you."

"P...please... I promise not to do it again."

"And what about the stock room and the jammed copier? Do you know how much
it cost me to get it fixed?" He shook his head. "You only have yourself to
blame, don't you?" More tears ran down his face as he nodded.

"Good, I'm glad you understand why I have to do this. Kick your shoes off
and remove your pants." His face pulled into a puzzled frown as he gave me
a pleading look as if to beg me not to make him do that. I just raised one
eyebrow and stood there waiting. With shaking hands, he unbuckled his belt
and unzipped his pants before kicking his loafers off and removing his
jeans. From reading some of his chat posts, I knew this felt more
humiliating to him, much as his father had made him feel when he was
younger.

Sitting on the edge of the couch, I drew him down across my lap,
immediately hooking my leg over his to prevent him from kicking and hurting
either of us. This time his underpants came down straight away, but I did
take my time working them over his quivering bottom. Once I had his
underpants arranged around his mid thigh to my satisfaction I ran my hand
over his baby smooth skin, feeling his stiffen at the touch. This time the
bare bottom paddle spanking was slow and deliberate to prolong his
humiliation as long as possible, but even so, it didn't take many swats
with the paddle to have him crying like a baby... or a sissy boy. He didn't
fight me as much this time, accepting this was his punishment for his
screw-ups. At some point, he must have lost track of where he was as he
suddenly blurted out something I hadn't expected.

"Please Daddy, don't spank me any more... I'll be good, I promise."

"I've hear that all before son and you still manage to screw up, don't
you." I answered, adding a few additional swats to his bright red bottom.

"Yes, Daddy... please stop... I'll do better... I'll behave." Whack --
whack- whack.

"Are you going to do as you're told from now on?"

"Yes, Daddy." Whack -- whack- whack.

"No more disobedience or arguing with me?"

"No Daddy I promise, I promise. Whack -- whack- whack. I stopped and pushed
him off my lap onto the floor between my open legs.

"What a little sissy you are crying like that. Stand up." He did, holding
his bottom to try and relieve the pain. "Take your underwear off, now!" He
didn't hesitate and immediately pulled his underpants off. I snatched them
out of his hand and throw them into the wastebasket.

"A sissy like you doesn't deserve to wear men's underwear, so from now on
you will wear these." As I spoke, I pulled a pair of very pink girl's
panties out of my pocket and held them up for him to see. He gasped in
shock and looked at me in horror.

"Ohhh please... no... not that."

"Do you want to go over my lap again for disobedience?" Jack quickly shook
his head and took the panties out of my hand. "The label goes at the back,
the yellow bow in front. Hurry up, I haven't got all night!" He jumped a
little and slowly stepped into them, reluctantly pulling them up his smooth
legs. The puffy panties were made of some soft silky material like satin
and had frilly white lace around the waist and leg openings. They also had
a yellow bow in front and long pink ribbons hanging down each side of his
smooth legs. I'd noticed that while he was lying over my lap, and thought
it a little odd that a boys of his age to have so little hair on his legs,
which suggested he had little or no hair on the rest of his body. So much
the better from my point of view as he wouldn't have to shave his legs when
it came time for him to start wearing stocking and a garter belt.

"P...please... sir. How long do I have to wear these?" He blubbered, fresh
tears of shame running down his face.

"Understand this, Jack. You aren't a real man crying like that from just a
little spanking. Only sissy boys cry like that, so you forfeited the right
to wear real man's underwear. From now on you'll wear sissy pink panties
all the time until you learn to stop crying, is that clear?" Slowly he
nodded. "Go and wash your face."

He turned and walked across my office to the toilet, rubbing his sore
bottom through the silky material of the panties. Rather than walk as a man
would, he walked on tiptoe like a girl, which was very appealing to
me. Either the hormones he was taking in his drinks was working, or the
spanking was making him walk like that. Either way, once he was in high
heels he'd look delightfully natural. I so dearly wanted to fuck his brains
out but held off, as I wanted to enjoy his descent into complete sissyhood
a step at the time. First, he needed to accept he was going to be wearing
panties for a long time, and that he was going to get spanked while wearing
them, deepening the feeling of shame and humiliation. Walking back in to my
office, still walking on tiptoe he came over and stood by my desk as if
waiting for my next order. Sitting behind my desk it was safe for me to rub
my stiff cock without him being aware of what I was doing. He did look
delightful standing there rubbing his bottom with both hands while looking
down at the floor in shame.

"I except you to be wearing those panties tomorrow at work, and I will
check. I also expect you to keep them spotlessly clean at all time. No wet
spots in the front, or other stains in the back. If I find any, you know
what to expect don't you." Jack nodded.

"Good. I also expect you to bring ALL your boys underwear to work tomorrow
in a bag for me to dump. I'll have additional panties for you to wear and
expect you to wear a clean pair each day, understand?"

"Y...yes, sir." He visibly shivered hearing that.

"Good, not put your pants and shoes back on and go home, and don't be late
in the morning." After dressing he left, but not before stopping in my
office doorway as if to say something. He didn't, just shook his head and
left. Even so, I could still see the tears in his eyes and wondered what he
wanted to say to me.

Much to my surprise, he went on line that night to the sissy chat room, and
admitted to another sissy boy that he'd been spanked. That chatted about
how much it hurt and how humiliated he felt being over a man's lap getting
spanked like a little boy. He even admitted he'd forgotten where he was and
called me Daddy, and how ashamed he felt when he realized what he'd
said. The other sissy giggled and said that he now had a `Daddy' to
discipline him when he needed it. After that, the chat degenerated into a
mutual jack off session while they called each other dirty names. I left
them to it as I had the information I needed. I did check the next morning
and found his swishing around the bedroom in his pink panties and looking
at himself in the mirror. He was obviously enjoying himself, reaching into
his panties every so often to jerk his cock a little.

Upon arrival at work the next morning, early before anyone else arrived, I
motioned him into my office and told him to drop his pants. He blushed
bright red but did as he was told, standing there for a moment with his
pants down and shirt up so I could inspect the panties. One look and I
could see a wet spot but didn't say anything. I knew it would grow by the
end of the day and give me good reason to punish him again. The fact that
he was already semi hard told me everything I wanted to know. Wearing
girl's panties turned him on, and with the soft silky material rubbing
against his cock all day would probably keep him dripping into his
panties. So much the better as it would set him up for the next stage in
his transformation into a complete sissy bitch boy. I took the bag of
underwear he'd brought and wondered how many he'd kept back. I'd find out
later today, and replenish this drinks. The fact that he'd brought them at
all told me a lot. For one he'd accepted his orders, which meant he'd
mentally submitted to me dominating him.



END PART ONE



`Bitchboy'



PART TWO



While he was nice and busy at the office I re-visited his apartment to make
sure he'd brought all of his men's underwear, but not surprised to find he
hadn't brought all of them. The colored unisex panties were still at the
bottom of his draw, in plain sight now the rest of his underwear was
gone. I turned his computer a little so I had a better picture of his bed,
but not so much as he'd notice. I added the cocktail to the new soft drinks
he brought to ensure his transformation would continue. I let the other two
temps go, as it was easy for me to send them back to the temp agency with a
glowing work report. It also meant that if I needed to bring more people in
during a rush, few would notice any changes in Jack's appearance. They'd
think he was always looked the way he did. At closing time, Jack locked the
office and came to my office, looking nervous and about to cry. The fact he
was holding his hands in front of his crotch told me something unusual had
happened.

"Put your hands on top of your head and come here." Let out a small sob he
did as I ordered, exposing a large wet spot in the front of his jeans. I
frowned as saw his start shaking.

"Did you pee your pants, Jack?" He shook his head. "Get those pants off,
right now!" I growled, seeing him shudder, but he obeyed and stood there
with tears running down his face. I walked closer and pulled the waistband
of the panties out and looked inside, knowing immediately what had
happened.

"I see, the dirty little sissy made a cumming in his panties, didn't he."

"P...please, sir. It wasn't my fault... it... it just happened." He
blubbered.

"And what were you doing or thinking to make you cum in your panties,
Jack." He blushed bright red and looked down at the floor. "Tell me the
truth, Jack or I'll spank you twice as hard."

"I...I was thinking about you spanking me..."

"While you are wearing your pretty pink sissy boy panties." He
nodded. "Were you touching yourself?"

"No... no sir I wasn't." I laughed then. The little pervert had cum in his
panties just thinking about getting spanked over my lap while wearing
girl's panties, how funny was that. "So, my little sissy boy made a cumming
in his pretty pink sissy panties?" I asked, brushing the back of my hand
across the front of his panties. I felt his cock jump at the touch, pushing
the front out to make a little tent. Jack sobbed and kept his eyes in the
floor. "I think the little cry baby sissy like being forced to wear pretty
pink girly panties, don't you Jack, or should I say Jackie."

"Oh god....no... I hate it. It's so humiliating being forced to wear them."

"Forced to wear what, Jackie."

"Panties, sir. Men aren't suppose to do things like that." He blubbered.

"But you're not a man, are you, Jackie, you're a little sissy cry baby,
aren't you."

"N...no... please, don't make me wear them."

"Wear what, Jackie. Say it."

"Please don't make to wear ....p...pretty pink sissy, girly panties, sir."

"Oh, I think they look perfect on a sissy crybaby like you, in fact I think
you should be wearing other things as well. Take your shirt and tee shirt
off.

"P...please no."

"Do it, or I'll double your punishment." He jumped at the sound of my harsh
voice and immediately started unbuttoning his shirt, crying as he did. A
few moments later, he was standing there in just panties and his sock with
his hands on his head, blushing furiously.

"Good, now you are ready for your punishment. Go and bend over my desk,
sissy boy."

"Oh god!" He turned and stumbled over to my desk and I was delighted to see
that he had small breasts already. They weren't big and he probably hadn't
really noticed them yet, but he would when I put the bra on.

"All the way over the desk, Jackie, hands behind your head." As he
complied, I ran my hand over his panty covered bottom, feeling him shiver
at the touch. I then ran my hand up his back, feeling the smooth hairless
skin under my fingers. I gripped the back of his neck with one hand while I
slowly pulled his panties down with the other until they fell around his
ankles. I then took them off, balling them up with the wet spot on the
outside.

"Open your mouth, Jackie." I ordered, pulling his head up by his long hair.

"Oooo please... don't..." Was all he managed to say before I stuffed the
panties in his mouth.

"You're keep those cummy panties in your mouth until I have finished
punishing you." Gripping his neck again and began spanking him with my
hand, hard sharp slaps to each cheek and his upper thighs.

Jack squeal around the panty gag and lifted his legs to try and relieve the
pain as I spanked him harder and harder. I expected him to fight me at some
point but he didn't and I knew he was mine then. Like it or not, he was
going to be my cock sucking sissy bitch boy and I was going to turn him
into a cock craving sissy faggot. Soon he'll be begging me to fuck his
sissy cunt, squealing and crying in shame as I fuck his sissy brains
out. He might hate it, but he wouldn't be able to help himself as the
feeling of shame and humiliation became a drug he couldn't get enough
of. The spanking done I made him stand in the corner for twenty minutes
sucking on the dirty panties while I got the rest of his sissy lingerie
ready and had myself a nice stiff drink.

"Come here Jackie." He came over on tiptoe, still with his hands on top of
his head and stood there obediently waiting for my next order. "Did you
enjoy sucking on your cummy panties, Jackie?" He shook his head.

"Then you'd better get used to it. Every time you make a mess in your
panties, or I find they are dirty, I'll put them in your mouth and make to
sit there at work for an hour. "Dirty little sissy boys like you need
discipline and need to learn to do what they are told, understand?" He
nodded again and I slowly pulled the wet panties out of his mouth.

"Seeing as you can't stop being a sissy cry baby, I think you need an extra
incentive to make you stop crying and act more like a real man." Saying
that I picked up the pink lace garter belt and wrapped it around his waist,
feeling him flinch as I did. Hooking the ends together, I snapped a small
padlock through the little stainless steel `D' rings so he couldn't take it
off. Next I put a pair of black, lace topped stocking on him wondering
again how a boy his age didn't have any hair on his legs. They were so
smooth the stocking slid up his legs without a snag. By now he was shaking,
fresh tears running down his face and I attached the stocking to the garter
straps.

"The garter belt always goes on this inside of the panties, unless they are
crotchless panties. In which case the garter belt goes on the outside,
clear?" Jack didn't know what to say except cry ever more. He reluctantly
stepped into a clean pair of sissy pink panties, the same as the ones he
had on all day. It was the bra that really got him sobbing at I put it
round his chest. The bra was what they call a `shelf' bra, as it just had
little cups to lift and separate the breast, leaving them and the nipples
exposed. As I suspected, with the bra on you could see that he definitely
had small girly titties. One look down and Jack gasped in shock.

"Oooo god.... Noooo..."

"Oh yes, my little sissy boy Jackie has little girly titties. Isn't that
nice." I murmured, cupping each small breast in my hand. I leaned down and
kissed each nipple, eliciting a small gasp from Jack knowing how tender and
sensitive they were right now. "Jackie is such a sissy, isn't he." Jack
just sobbed in shame and I tweaked the nipples. To make him cry even more,
after which I deliberately fiddled with the small padlock before turning
him around and snapping it closed on the `D' rings, locking the bra to
prevent him removing it.

"Put your jeans and shirt back on, Jackie."

"P... please, sir... the tee shirt?"

"No, only real men wear tee shirts. Jackie, and you're no longer a real
man, so you can't wear it."

"Not ever?"

"No, not ever. You will only wear the shirt from now on."

"B... but... everyone will see I'm wearing a bra, sir." He sobbed.

"That's right, and know you are a sissy panty boy."

"Oh god... please... no."

"Do you want me to put you over my knee and spank you again, Jackie?" He
shook his head.

"Good, go wash your face before you go home. We don't want everyone seeing
that you're a cry baby as well, do we." Jack shook his head and stumbled
off to the bathroom to wash his face. I knew I had him now, as he hadn't
fought me or taken the opportunity to leave when he had the chance. Now it
was just a question of feminizing him even more. Very soon, he'd be coming
to work wearing girl clothes and looking like a girl... well, like a
crossdressing, cum sucking sissy faggot at least. He came back in and I
held out the wet panties."

"Takes these home. I expect you to wash them clean, dry and iron
them. Bring them with you to work tomorrow, understand?"

"Please don't send me home like this." He sobbed.

"There, there, sissy boy," I took a tissue, and lifting his head I wiped
his eyes dry, "this is for your own good, Jack. You have to learn to stop
being such a sissy when you get punished, don't you?" I drew him against me
and stroked his hair and he sobbed on my shoulder.

"Please."

"Come on, admit it, you know you deserved the spanking, didn't you." He
nodded against my shoulder. "And you have to learn not to be such a sissy,
don't you." He nodded again.

"Yes, sir." He answered, barely audible.

"Good, off you go sissy boy and drive carefully, you don't want to get
pulled over by the police, do you." He took a shuddering breath and shook
his head, a trace of tears in his eyes at the thought of a cop seeing him
dressed like this.

I smiled to myself as I pour another drink. Things were progressing a lot
faster than I imagined, expecting more of a fight from him as I stripped
him of his manhood, what little he had left that is. He'd obviously been on
a descending path into sissyhood for a while, maybe since his high school
days, or maybe before that even. Whatever the cause I was reaping, or
raping the benefits of that. It was clear that he'd end up as someone's
bitch boy so it might as well be me to start. As I expected the little shit
went on line the moment he got home after stripping off his pants and
shirt. He stood for several minutes in front of a big mirror just looking
and touching himself, especially his little girly titties, as if he
couldn't believe they were actually there. Several time he let out a sob,
so I knew he was still feeling the shame and embarrassment of having
titties. I smiled at the thought that he might be thinking that was the end
of it. He didn't know it, but before long, he'd be in a dress, or a skirt
and blouse as well and be sent home that way. I was going to humiliate him
so much he'd never lift his head and look another man in the eyes unless
ordered to. His on-line chat session was short and sweet, as his sissy
friend wasn't on-line tonight so he logged off and pranced about, hand
washing and drying his pink panties. He did take his time ironing them and
making sure the ribbon were straight and wrinkle free. He might whine and
protest that he hated being turned into a sissy, but the way he carefully
ironed those panties told a different story. My guess was the he loved and
hated being forced to wear them and his other sissy clothes but he was to
the point where he couldn't help himself now. Hate it as much as he liked,
he knew he'd was going to be forced to wear them and that turned him on by
the erect state of his little sissy cock inside his panties. He did take
care to remove them so as not to get a wet spot inside, and by nine o'clock
he was in bed jacking himself off to some dirty erotic fantasy. I just
wished I knew what it was so I could force him to relive it.

He did wear a light jacket the next day and I didn't force him to take it
off even though we were the only ones in the office right then. People did
come in to ask question, and Jack's desk was up front so he was the first
person they talked to when they came in. Depending on what they wanted, he
would either call me, or bring them back to my office. I did ask him to
come in at break time and give me the panties, taking my time to examine
them, causing him to blush a lot.

"Are the ones you are wearing still clean and dry, Jackie?" He gulped.

"Y...yes, sir."

"Come here." I motioned him to come round the desk and without asking I
undid his belt and unzipped his pants. The pants fell down around his
ankles as I felt the budge in his panties and ran my hands up and down his
stocking covered legs, leaning forward to look. He gasped for breath as I
touched him and started shaking, as his sissy cock got hard.

"Is my little sissy boy getting a stiffy from me touching him?"

"Ooooo... please... don't." He begged as his little cock pushed the front
of his panties out. What made it worse for him was the fact that my office
door was open and the front door unlocked. Anyone could walk in or look
through the window and see him like this. That he also had a wet spot in
the panties didn't help.

"What a naughty sissy boy you are, there's a wet spot in your pretty
panties."

"Please, sir... I can't help it." He hiccupped.

"I know, Jackie, that's what happens to sissy boys when they wear pretty
pink panties." By now, I was gently squeezing his cock through the silky
material. "Would you like to jack off like you did last night in bed?" He
shivered and nodded. "Yes, I know you would. Take your pants off and go
lock the front door." Jack whimpered but did what I told him, quickly
pulling his pants off and almost running to lock the front door. When he
came back, I pulled him over to the couch and sat, pulling him down to sit
on my knee.

"Such a naughty little sissy, aren't you Jackie, prancing thought the
office in your pretty panties and slutty lingerie."

"Oh god... yes... sir." He moaned and I ran my hand over his panty-covered
cock.

"That's a good sissy. Stand up and pull your panties down so I can see you
little sissy cock." He let out a shuddering breath as he stood and slowly
pulled his panties down until they dropped to the floor. His cock stuck
straight out, as stiff as a bar. I pulled him back down to sit on my knee
and pushed his legs open wide.

"Tell me what a dirty little pantyfag you are, Jackie."

"Oh god... I'm a dirty little panty wearing sissy boy." He sobbed as I
stroked his cock.

"Aren't you ashamed of yourself being forced to wear girl's underwear and
lingerie?"

"Yes, sir, very ashamed. It feels so humiliating have to wear this and come
to work in it."

"And so you should be. A real man wouldn't wear this would be?" I asked,
tugging at the garter strap.

"No, sir, a real man wouldn't."

"Tell me what sort of man would, Jackie?" Panting for breath, he gulped out
the answer.

"A pathetic little panty wearing sissy faggot, sir." He sobbed as I worked
the foreskin of his cock back and forth faster.

"Is that what you are now, Jackie?"

"Oh god... yes sir." He cried, bucking his hips back and forward in time
with my strokes.

"Good sissy, now give me a panty wearing sissy faggot kiss." He almost
squealed as I forced his head around and pull it down. His lips locked onto
mine and I slipped my tongue into his unresisting mouth. It was too much
and he suddenly exploded, shooting a long, thick stream of cum across the
carpet, moaning into my mouth as he climaxed. He slumped, spent for the
moment as I held him, and stroked his hair.

"There, there. Don't you feel better now you've admitted what you are?" He
nodded against my shoulder. "Good, put your pretty faggot panties back on
and go get a towel to clean up this mess. Sissy boys shouldn't waste cum,
Jackie. I'm going to teach you not to waste it from now on." Jack blushed
bright red and pulled his panties back on before running to the bathroom
for a towel.

Now I had him and there was no way out for him. Today he'd learn what his
main function in life was from now on. I suspected it would take a few good
spanking to make him comply, not that it mattered, I like spanking my sissy
bitches. I thought of taking him home and fucking his brains out right then
and there, but resisted the temptation. I wanted him in a position where he
had no choice but to submit to whatever I wanted.

That evening I had an idea how to get into his mind and quickly went to the
sissy chat room he went to. It took a while to get in, having to sign in
with a user name. I put down `strict DOM' and filled in the other bullshit
to get into the site and sat watching him for a while. I had to ignore
several request to chat while I waited until he finally came into the
bedroom and got undress. Once stripped he stood looking at himself,
touching his cock and pinching his little nipples until at last he sat and
logged in to the chat site. He didn't have a particularly sissy screen
name, just `Curious sissy' but I waited to see if he'd PM me. He didn't, so
I sent him a private message asking him if he wanted to chat. He quickly
answered that yes he would, so I PM him into a private room.

"Hi sissy boy." I greeted him, glad to see him sucking on a bottle of
orange juice.

"Hi, sir."

"What's your sissy boy name?"

"Name? I don't really have one."

"You should. All the other sissies on here have one."

Lag

"I've never really thought about a name, sir."

"How about Crystal, would you like that?" I saw him smile on the other
screen and knew he liked it. It probably made him feel more sissy.

"I like that, sir."

"Good. I'll call you Crystal from now on. You can call me sir or Daddy if
you'd like. I'm a very strict Dom and don't like sissyboy lying to me."

"I...I'll tell you the truth, sir."

"Good. How long have you worn panties and been a sissy?

Lag

"Not very long, sir. I just started recently."

"How old are you?"

"I'm 20, sir." He lied, but I let it go. Some sites have a strict policy
about age.

"You start wearing them by yourself or did someone put you in panties?"

"A bit of both... I like to wear sort of girl's panties occasionally,
but...but... this guy I know forced me to wear real panties."

"He forced you?"

"Yes, he forced me to wear these things. It's so humiliating."

"These things? What else has he forced you to wear?"

Long lag.

"Come on, tell me the truth, what else has he forced you to wear?"

Lag.

"He makes me wear a garter belt, stocking... and... and a open bra (sob)."
The sob wasn't faked as I saw his chin start to quiver.

"If you hate wearing that so much, why don't you just take it off?"

Lag.

"I can't... he locked them on me (sob)."

"How did he force you to wear panties?"

Lag

"He spanked me."

"Spanked you... hard?"

"Yes, very hard."

"And so?"

"I started crying and he said that only sissyboy cry at being spanked, and
he made me wear the panties as extra punishment." I hadn't put it that way,
that was something he'd come up with as an excuse to cover how pathetic he
was at letting me put him in them in the first place.

"Oh I see, you're one of those reluctant sissy boys that have to be
forced."

"I...I'm not a sissy... I'm a man. I just like to put panties on once in a
while to play on line." He glared at the screen as he typed the words.

"Ha ha ha. Bet you think you're a real man, don't you, sissy Crystal."

"I am." He shot back.

"No you're not. Tell me what real man would wear panties, bra, stocking and
garter belt to work?"

"To work?"

"Yes, to work. If they are locked on that means you have to drive to work
wearing them, don't you." Long lag and I could see him biting his lower lip
as if thinking what to answer.

"Come on. Tell me what real man would do that."

"A real man wouldn't do that (sob)."

"That's right, only sissy queer boy and panty fags do nasty things like
that, don't they."

"I'm not."

"Yes you are. I bet you secretly love being forced to wear slutty girl's
underwear, don't you."

"No... its... it's so humiliating and I feel so ashamed having to do that."

"Yeah, of course you do, that's why you're sitting there in pink panties
touching yourself."

"I'm not touching myself, honest."

"Liar. I bet you even have a little stiffy in your panties, don't you,
sissy."

"No.... yes." He retyped.

"Thought so. Stop touching yourself and pay attention or I will leave."

"Yes, sir."

"That's better. How big is your little sissy cock?"

Long lag.

"It's...its only five inches when I'm hard. Sir."

"Ha ha ha ha. That's not a cock, that's a sissy clitty. With a little cock
like that, it's no wonder you're a sissy queer boy. I've seen girls with a
bigger clitty than that."

"I'm not, honest (sob)."

"Bet you've never even fucked a girl, have you."

Long lag.

"No, sir I haven't."

"Thought so, not that a little cock clitty like that would be any use to a
real woman, a little girl's maybe, or another sissy boy."

"Oh god." Jack's face was red now, so I knew the verbal humiliation was
turning him on. I saw him reach down and play with his cock a little and
knew he had a stiffy in his panties.

"Has this guy put you on your knees and fucked your mouth, or bent you over
and fucked your tight sissy cunt yet?"

"Oooo... no sir he hasn't."

"Bet you've thought about him doing that, haven't you."

Very long, lag this time.

"Yes... I've thought about him spanking me and forcing me to suck his big
cock." I could see the shame on his face as he typed that. Being an
anonymous chat room, he thought he could say that without consequence.

"And bending you over and fucking you?"

Long lag this time.

"Come on, tell me the truth, it's what I'd do to you."

"Yes, sir... you would?"

"Yes I would. I'd spank you to tears then put you on your knees where a
sissy like you belongs and forcibly fucked you warm wet mouth with my big
hard cock." I saw him shiver and knew I was getting through to him
now. "After that, your tight sissy pussy would be mine and I'd fuck your
little sissy brains out." Jack had his hand inside his panties furiously
jacking off.

"Oh god!"

"Yeah, I'd soon have you dressed up all the way like a dirty little sissy
faggot, prancing around and sucking and fucking whenever I wanted to take
you, willing or unwilling."

"Oh god... you wouldn't."

"Why not, you're a failure as a real man; you're useless to a real woman,
so that else is a pathetic little sissy like you is good for but being put
in panties, put on your knees for a real man to forcibly fuck your sissy
bitch boy mouth."

"Oooo god!" he sobbed.

"Yeah. I would. I'd force fem you into a girly boy and pimp you're sissy
ass out to dirty old men to fuck for money whether you wanted to or
not. Once I'd have you addicted to cock you wouldn't be able to help
yourself sissy bitch."

"Ooooo god noooo!" He squealed as he came in his panties.

"Did the dirty little crossdressing faggot just cum in his pretty pink
panties?"

"Yesssss."

"Good, now fuck off and clean yourself up, bitch." I quickly signed off
just to leave him hanging and feeling ashamed of himself.

For a moment, he just sat that with tears running down his face, then dived
onto the bed and buried his face in the pillow and pulled the covers up
over his head, sobbing his eyes out. I suspected he knew he how pathetic he
was for what he'd just done. He just didn't want to admit it. I did like
the reluctant sissy boys best as they were so much more fun to train than
the willing ones. Even when fully converted into cock sucking sissy faggot,
they still remembered they were once a real man, and that made them even
more desirable to men who like to force them to fuck or suck.

The next day he looked a little miserable and as if he hadn't slept very
well last night. So much the better. His willpower would be low and less
able to resist me. To add to his discomfort I ordered him to take his
jacket off by saying that no one could see the bra he was wearing due to
the blue shirt he had on. It was partly a lie, as you could faintly see his
bra and little titties. Later, once he realized his bra and titties could
be seen his feeling of shame would be deeper. Several people came in asking
question about drafting rates and such, and a couple of guys even came back
to ask additional question. I smiled seeing that, as I knew they'd seen the
bra and titties and came back for another look at the swishy little sissy
faggot. The next day went pretty much the same way, but a few guys came in
for no particular reason, guessing they came in to look at him. Once he
realized people could see what he was wearing, he tried to wear a sweater
to work, but by switching off the AC off and telling him it was broken, so
he soon had to take it off. I didn't bother playing with him on line as I
thought it time to take him to the next step and put him on his knees where
he belonged.

"Lock up Jack, and come into my office." He shot me a soulful look and went
off to lock the front door.

"Strip down to your sissy underwear." I said over my shoulder as I lowered
the blinds. I turned and watched him slowly undress, feeling myself harden
as his slutty lingerie came into view.

"I'm very disappointed in you, Jack. You work the last couple of days has
been less than acceptable." He let out a hiccupping sob.

"Please, sir. I did my best."

"Your best is far from being what I expect from you." Sounding stern and
commanding as I laid the paddle on my desk.

"Oh god... please no... not the paddle." He whimpered.

"Your choice Jack. A spanking or you leave. Which is it?" Already down to
his slutty underwear is wasn't as if he had a choice.

Well he did, but I suspected he'd already accepted he was going to get a
spanking so leaving wasn't an option for him. Walking over to the couch I
sat, motioning him closer, spreading my legs so he could stand between
them.

"Kneel down, Jack." With a little sob he did, flicking quick glanced up to
my eyes. I smiled at him and stoked his hair for a moment. "You know this
is for your own good, Jack, and you know you deserve it for your poor
performance, don't you."

"Please..."

"Say it Jack. Tell me what you did and what's going to happen." Tears
started running down his soft face.

"You're going to spank me for poor work performance."

"Sir."

"Sir." He repeated as I slipped my hand behind his neck and slowly forced
him over my knee. He knew the right position now and slipped over until his
hands were on the floor and his panty-covered bottom was in the perfect
position.

"That's a good boy, Jack. You know you deserve this, don't you?" I asked as
I ran my hand over the silky material over his quivering bottom.

"Y...yes... Daddy." He sobbed as I hooked my thumb into the waistband of
his panties. I slowly worked them down over his bottom to mid thigh, each
side a little at the time to prolong his humiliation. The further they went
down, the more he cried, as if some secret damn inside him had failed. He
hated this but the feeling of humiliation was so strong he couldn't stop it
from happening.

"You are such a little sissy crying like that before I've even started
spanking you, aren't you Jack?"

"Oh god... no... please."

"Say it Jack. Tell me what you are."

"I...I'm a pathetic little sissy, Daddy."

"And what are pathetic little sissy boys good for, Jack?" He started crying
harder if that was possible.

"Nothing Daddy. I'm a failure as a man and no good to a real woman..." He
stopped and sobbed.

"Go on, what else?"

"I'm only good for putting in panties for a real man to use like a slut,
Daddy."

"Very good. Maybe I won't spank you so hard tonight after all."

"Please, Daddy, don't spank me so hard." Dream on sissy boy. I was going to
strip him of the last bit of manhood he had tonight.

I started spanking him with the paddle then, slowly and lightly at first,
just to warm up his sissy ass. After a while he started bucking and
shrugging but it was half hearted at best as I continued. His last feeble
attempt to assert his manhood failed, as I knew it would and I knew he was
ready for the next step in his descent into sissyhood. I pushed him off my
lap at last to kneel between my legs and lifted his head to dry his face
and eyes while he rubbed his sore bottom.

"What a pathetic little sissy you are, Jack. Stand up on your knees." He
did, and I reached down to feel his cock and caress his balls. "Even your
little cock tells me you are a sissy boy. This is what a real man's cock
feels like." Saying that I took his hand and placed it on my stiff cock. He
moaned, but whether in shame of excitement I didn't know. Why is it you
have a stiffy, Jack? He just shook his head, unable to answer.

"Feel it Jack. Feel what a real man's hard cock is like." Jack shuddered
but did what I told him, gentle squeezing my cock though my pants. "Yeah,
that's it. Maybe the sissy boy wants to see it as well as feel it." Jack
shook his head and sobbed as I stood. Unzipping my pants I let them drop to
the floor and stepped out of them. "Feel my cock, Jack." I ordered as I
kicked the pants aside.

"Please.... No..." He sobbed, knowing what was coming next. His shaking
hand reached up and grasped my cock through my underwear, unable to pull
his eyes away for the big budge under the white jockey shorts.

"Come on sissy boy, get it out. Pull my underpants down and get your hand
around it!" Jack whimpered but didn't let go of my cock. I took his hand
away and pushed my under pants down myself and kicked them off. I was so
hard it was almost painful and the tip of my cock was no more than three
inches from his lips. I ran my hand through his hair and stroked the side
of his face, much as I would if he was a girl kneeling there about to get a
mouthful of my cock.

"Get your hand around it Jack. Play with it. See how big it is compared to
your pathetic little sissy clitty." Jack just sobbed and moaned out loud
but did what he was told. I don't think he could help himself anymore as he
began to jack me off. It felt so good having him do it and gripping his
hair I slowly pulled his mouth closer.

"Oh god... please... no."

"No what, Jack. Look up at me." He tore his eyes away from my cock and
looked up at me with pleading eyes.

"P...please... don't... don't." He could hardly get the words out. "Please
don't make me put it in my mouth." He sobbed, hot tears of shame running
down his puffy, red face from so much crying.

"I won't Jack. It's your choice. This is part of your punishment
today. Either you put my cock in your mouth or you go back over my knee to
continue the bare bottom spanking." Jack dropped his eye and sobbed as he
shook his head. His tight little bottom was already bright red and still
stinging from the last spanking.

"Look up at me and open your mouth, sissy boy."

With one last desperate appeal with his eyes as he looked up, Jack slowly
opened his mouth. Holding his hair tight, I pulled his head towards me and
watched as the head of my hard cock vanished inside his wet, warm mouth.

"That's a good sissy. Get your lips around the shaft of my cock, nice and
tight. Just like a young girl's pussy." I breathed, reveling in the feeling
as I started pumping my cock in and out of his mouth.

Jack grabbed my thighs and tried to pull away, whimpering and trying to
squeal around my cock. Failing that, he start beating my thighs, but
strangely not that hard. Maybe it was his last attempt to exert his manhood
as I raped him mouth, not that I cared at that moment, the little fucker
was going to get his first mouthful of man cum and be forced to swallow
it. I would love to get my cock all the way in his mouth and shoot the cum
straight down his throat into his belly, but I'd do that once he was
addicted to the taste of cum and the humiliating feeling of it filling his
mouth. I slapped him on the back of his head when I tried to talk around my
cock.

"I said wrap your sissy lips around the shaft, bitch, or do you want me to
beat you again?" Jack shook his head and cried, but he gripped my cock
tightly with his lips. Now he'd stopped beating my thighs and simply held
them tight, squirming and wiggling his bottom as I speeded up. His mouth
was delicious and much to my surprise I got more of the seven inches inside
without his gagging. I slowed and still holding his head tight I gently
slid my cock in and out, going a little deeper each time. He let out a
muted squeal as I push all seven inches inside his mouth and down his
throat without him gagging at all, but I pulled back out so he could
breath.

"Lick my cock, sissy bitch. Lick it all over like a good little faggot."

"I'm not! I'm not!" He blubbered.

"Lick it, bitch!"

"Nooo."

I didn't hesitate and pulled him over my knee as I sat down. Holding him
tightly, I spanked his bare bottom ten time very hard with the paddle as he
lay there squealing and sobbing.

"You going to do what I tell you, sissy bitch?"

"Oh god... yes... don't spank me any more... please... I'll do it!" I
pushed him off my lap onto the floor between my legs and grabbed him by the
hair and pull him in. My cock hit his mouth and he immediately started
licking. I guided his head so he licked it one side, then the other, then
underneath.

"Take my ball in your mouth and wash them, cunt!" He squeal but did what I
told him and sighed with pleasure. As much as he cried and squealed he did
a good job of washing my balls. Once he'd done that I pulled them out of
his mouth and slid my cock back him, this time he hardly resisted my
violation. He even wrapped his lips tightly around the shaft as I moved his
head up and down, having learned the consequences of disobedience. It
wasn't long before I felt myself nearing a climax and stood, wanting to
really fuck his mouth properly before I shot my load.

"Oh yes! Now the little fucker knows what he's good for. I'm going to drain
my balls into your sweet mouth, Jackie boy and you're going to swallow all
of my hot, dirty cum." Panting for breath I pumped my cock in and out,
trembling with excitement and the feeling grew. "Oh yes! Here it comes you
little fucker, suck my dick faggot, suck all that hot disgusting man cum
out of my cock." And suck he did, gripping my thighs as if hanging on for
dear life.

"Ohhhh fuck yesssss." I groaned as my cock exploded and flooded him wet
mouth with hot cum. "Swallow it, sissy bitch, swallow it all." I panted,
pushing his head back so the cum ran to the back of his throat. In that
position he couldn't help but swallow, squealing between throat contraction
as he swallow my cum. The little sissy faggot was mine now and knew what
was expected of him from now on. I left him kneeling there while I went to
the bathroom to clean up, finding him still there when I came back. I
grabbed my shorts and pants and got dressed before sitting down in front of
him again. Grabbing some tissues, I lifted his head and wiped his face dry
and looking him in the eye. I could see the shame and humiliation there,
and something else.

"Stop crying sissy boy. Your punishment is over for today." I murmured
softly. He nodded and tried to look down.

"You be a good boy and not fuck up again, and I won't have to punish you,
will I?" He shook his head.

"N...no... sir... Daddy." He whispered. I kissed him on the lips then, and
strangely he didn't try to pull away.

"You go and clean up, get dressed and I'll take you out to dinner, okay?"

"Y...yes, sir."

"You can call me Daddy if you'd like. I kind of like it." He gave me a weak
smile and carefully stood and pulled his panties back up before swishing to
the bathroom.

All in all I thought it was a good evening. Jack now knew his place in life
and it was up to me to reinforce it. I doubted he'd give me any more
trouble, other than the token resistance, which was so much the better. It
made it more fun for me so for a while I'd let him go back to thinking he
was a man to some degree. It would take a few day for him to get over what
happened and convince himself it wasn't his fault. He'd use the excuse that
I forced him to go it, so that meant he wasn't cock sucking, sissy homo
faggot really. He didn't say much during dinner, not that I expected him to
and he still felt ashamed about what had happened. I managed to get several
drinks inside him to the point I drove him home to my place and put him to
bed in the spare room. I did strip off all his lingerie, and slipped on a
pair of his unisex panties. Little did he know it, but he'd be spending a
lot of time here shortly, but first I had to arrange a few things, like his
getting him evicted from his apartment. The next morning after breakfast
and a blushing `good morning' we went to work as usual, and I got things
underway.

I knew for telephone calls that he was behind on his rent and car payments,
and with a little careful sleight of hand with the mail, I could arrange
for him to be evicted. Every two week he had to send his time sheet to the
temp agency and he trustingly gave it to me to sign and mail. Of course I
kept the copy of the time sheet and didn't bother sending it in. That of
course meant the agency had to call him several days later and tell him to
send it in or he wouldn't get paid. He came to me in a panic and asked if
I'd sent it in, and I assured him I had. That caused his paycheck to be
delayed by a couple of weeks before it was sorted out and by that time his
landlord posted a three day eviction notice on his door. With all his stuff
piled into the car, he came to work late and tearfully told me the story. I
was sympathetic and said that he could stay in the spare room at my place
for a while until he found another place to live. I told him the rules
about keeping his room tidy, and the consequences if he didn't. That made
him blush, as he knew I meant it, and what those consequences were. It
ended up that his paycheck was delayed a month and they repossess his
car. He never thought it odd the repo company knew where to find it. Now he
was dependent of me for food, lodging and transportation to work, now for
the next step in his entrapment. Of course he didn't keep his room clean
and tidy as instructed and by the third week I took him to task over it
after dinner one evening. Me putting the paddle on the coffee table told
him he was in trouble again, but I did think it a little odd that he'd
disobeyed my orders by not keeping his room clean and tidy.

"Go take a shower and put your sissy panties on and come back here, Jack."

"What... I didn't... I meant what did I do?" he asked, seeing his chin
quivering as he spoke.

"What did I tell you about keeping your room clean and tidy?"

"Oh god... please... I'll go do it..."

"You will after, now go and do what you're told!" He scampered off, already
sniveling.

I poured myself a drink and sat on the couch contemplating how far I'd go
tonight. As usual, I was wear shorts and a white muscle tee shirt and no
underwear, so by now he'd got accustomed to seeing me like that in the
evening. The fact his eyes were looking at my cock under the shorts more
than he should told me he was thinking about what happened the last time I
punished him.





























"Have you ever been to a spar, Jack, or had a facial?" I asked casually.

"No, sir I never have. My mother used to go to the spar once a month. She
had a manicure and a pedicure, massage and have her hair done."

"Good, I'm going to take you to a spar and have them give you the
works. Would you like that, Jackie?" He blushed hearing me use his sissy
name but looked a little unsure.

"You'll feel so relaxed after the massage."

"Okay, sir, when?"

"I'll pick you up at your apartment tomorrow morning at eight. I'll unlock
your underwear so you can take a shower in the morning before I pick you
up. Just where a pair of short, a tee shirt, and sneakers, clear?"

"Y...yes, sir."

"Good, get dressed and go home." Murmured in his ear as I undid the
padlocks on his garter belt and bra, feeling more than hearing him sigh,
and probably thinking how he could go to bed tonight without them.

He quickly dressed and rushed out of the office, wanting to get as far away
from the scene of his disgrace as soon as possible. I knew the feeling of
deep shame had kicked in, and with his mood swings due to the hormones he
was taking, he'd probably cry on his way home. So much the better, as
humiliation is like some erotic drug to a sissy. He just couldn't get
enough of it, no matter how much he protested and denied he hated it. For a
lot of closet sissy queerboys, the thought of being force femmed had a
special attraction, and an even deeper feeling of shame for letting it
happen. That was second only to being `outed' or being forced to go out in
public dressed in his sissy clothes for all the world to see. Fear of
exposure, especially to his parents, relations, and friend held a special
fear in a sissy boy's soul. Once done he knew he could never go back to
being who he was and hiding behind his pretend manhood. Tomorrow, all those
fear would come together and he'd be trapped and mine for the taking.



END PART TWO





START PART THREE



`BITCH BOY'



I deliberately park in the street outside his apartment a little early and
waited, seeing him exit his place and walk along the upper walkway to the
stairs. He saw me and waved, recognizing my car. Parked where I was he had
to walk by the pool and even this early on a Saturday there was several
guys and a couple of working girl lounging about the pool. I say walked,
but he sort of swished, walking on his toes rather than flatfooted as most
men do. I noted several older men eyeing him up as he tripped by and knew
they all wanted to rip his shorts off and fuck the living shit out of the
little queer. I smiled, that honor would be mine by the end of the day. He
slipped into the passenger seat with a sigh, blushing slightly and looking
down without realizing how seductive that was.

"Good morning, sir."

"Good morning Jackie, did you sleep well?"

"Yes, sir."

"Good, just relax while we take a little drive across town."

The drive to the spar I knew that catered to the TG set wasn't long in the
light traffic in Hollywood at this hour. Pulling into the parking lot he
followed me inside where the beautiful woman who owned and ran the place
greeted me. Other than a slight hardness around the lips and eyes, few
guessed she was actually a `he', a transsexual. `She' ran the place like a
military barracks and didn't permit any sexual high jinks between the staff
and the patrons on the premises. It was her way for keeping the place off
the police radar and she'd only been raided once in ten years, and that was
just after she opened the place. If any of the staff and patrons wanted to
get together, they did it elsewhere and that was none of her concern.

"Nice to see you again, Mr. Franklin."

"Nice to see you gain, Crystal. This is this young man's first visit to a
spar, so treat him gently." I smiled.

"We treat all out guests gentle." She answered. "So what is his pleasure?"

"Oh, he wants the works." I answered winking at her where Jack couldn't
see.

Not that it mattered as his attention was on the beautiful young females
walking about in the tight, white shorts and tank tops. Little did he know
they were all TG, or TS's as were most of the staff and guests. Crystal led
us to a changing room and motioned us inside.

"Please undress and put the robe on you'll find behind the door, and I'll
come and get you in a few moments. Oh yes, before you get undressed, please
drink this." She said as she poured a greenish liquid into a glass from a
bottle she took out of her gown. Jack looked at me and I shrugged.

"It's just grass extract and juice. They believe in a healthy diet here and
it's part of the treatment." Jack looked at it suspiciously but did as he
was told and drank it all as Crystal departed.

I waited for him to start undressing before doing the same myself, as I
needed to get a sauna and a massage myself.  Jack stripped off his tee
shirt first, then pulled his shorts down and much to my surprise he was
wearing a pair of the colored unisex panties he had hidden in his draw.

"Those to, Jack."

"But..."

"Don't argue. Take them off. You'll be going to the sauna first, then the
pool before your massage so you won't need them."

Saying that I dropped my shirts and casually put the robe on, seeing him
look at my cock out of the corner on my eye. He gulped and blushed, as my
seven-inch member put his little sissy cock to shame. He quickly grabbed
the robe I held out for him and put it on to cover his semi stiff cock. I'd
have loved to know what he was thinking at that moment to give him a
stiffy, but that would have to wait. Crystal returned and led us to the
small, individual sauna.

"You are in number three, Mr. Franklin, and you will be in number four. If
you should need to go to the toilet in the next half hour, you'll find a
stall at the end of the bench." She handed us each a bottle of water,
smiled and left us to it.

I knew Jack would be sitting on the toilet very soon as the greenish liquid
did its work to clean him out. The water had an added ingredient and very
soon, he'd start to feel sleepy once he drank it, and he would with the wet
heat in there. I only stayed in the sauna for ten minutes before exiting to
find Crystal waiting for me.

"He's nice looking, but once we've finished with him he'll look ever
nicer. New one is he?"

"Yes, very new and very virgin."

"That's good, we need a few news faces around here. She laughed. "I take it
you want me to give him a full make over?"

"Yes, the works. I have his new clothes in a bag in the truck of my
car. Would you have one of the `girl's' get it for you."

"I'll take care of that. You go and have your usual massage and I'll take
care of little Jack." She looked at her watch. "I'd better check up on
him. Don't want him falling sleep in there." She looked in and nodded to
me, and a moment late came back out supporting Jack and he stumbled
out. Now the fun would start so I relaxed and went off to get my massage.

After, I took a long cool swim and a shower before getting dressed and had
a light lunch out on the patio, chatting to one or two people I knew over a
nice glass of wine. At last Crystal signaled to me that Jack was ready to
go, and saying goodbye I walked out to the car supposing Jack by his arm as
he was almost awake now. Settling him into the passenger seat I made sure
his seat belt was secured and drove away, smiling to myself. The new Jack,
or Jackie now was a lot different from when I'd taken him in. His shoulder
length hair was now cut and shaped to frame his soft, girlish face and now
a horny blond with golden blond ends. His ears were pierced with two-inch
long gold strands hanging from each ear. His eyebrows were plucked into a
nice thin arch and he had his eye lashes lengthened and now a jet black to
contrast with his power blue eye shadow and thing black eye liner. I
particularly liked the frosty pink lipstick he was wearing, the lower lips
having been glossed to make it look more inviting, which it did. Overall,
his face was much softer and girlish now, what with a few collagen
injections around his eye, lips, and the bridge of his nose to soften the
outline of his face. His lips were definitely fuller now and had a slight
pouting look that I liked. He'd soon find out that the makeup didn't wash
off and took a special solution to remove it, again trapping him into his
new persona. I could clearly see the black lace, open bra and his redden
nipples under the loose fitting, sheet white blouse, and I knew he was
wearing black lace crotchless panties and a black lace garter belt under
the short tan mini shirt he had on now. I could also see the tops of his
black stocking, but I particularly like the strappy black high heels he was
wearing as I could see the frosty pink nail polish in his toe nail that
match the color of his finger nails. All in all it was a sweet package, and
I was looking forward to seeing his reaction when I got him home and he saw
himself in the mirror for the first time.