Date: Fri, 13 Jan 2017 22:28:48 +0000 (UTC)
From: Robin Buckman <pink_pantyboy@yahoo.com>
Subject: Bitchboy - Part Two

`Bitchboy'

By

Pink_pantyboy

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 and bra on and come back here,
Jack."

"What... I didn't... I mean, 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 wore 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. The little fucker came tripping back in a short while later,
smelling all fresh and sweet from the body wash I'd left in the shower.

"Get me a refill, Jack." I said, holding my glass out, wanting to see his
cute little ass in those pink puffy panties rather than another drink. He
swished his way to the kitchen without realizing the show he was putting
on. His little girly titties were definitely larger now, but still not full
tits yet, more like those you'd see on a 12 or 13-year-old. He came back in
with a fresh drink walking on tiptoe as he was want to do now, and with his
shoulder length hair he looked ever more like a girl than a boy now. Taking
the drink he offered, I pointed to the floor between my legs and he
obediently knelt.

"P...please... Daddy, don't spank me. It hurts." Chin quivering, eyes wet
and glittering."

"Jack, you know very well you deserve to be spanked, don't you?"

"Y...yes, Daddy."

"So, are you going to behave yourself and take your punishment, your full
punishment like the sissy you are?" He nodded, knowing full well what I
meant. I took a stiff gulp of my drink before setting it down on the coffee
table beside the couch.

I hardly had to touch the back of his neck before he was sliding over my
lap and settling himself in the right position. At least he'd come to
accept this and I no longer need to hook my leg over his. He even wiggled
closer to my body and my hard cock pressing against his side. He now knew
spanking him turned me on and I suspected he took a perverse pleasure
felling my hardness pressing against him.

"What a little sissy you are, Jack. Prancing around in your pretty pink
girly panties."

"Yes, Daddy."

"I think you enjoy me forcing you to wear them, don't you."

"N...no Daddy. I feel so ashamed when you make me wear them to work. The
nasty men who come to the office can see I'm wearing a girl's bra."

"I know, and they get so hard seeing you like that." Jack moaned. "I bet
most of the would love to fuck you or have you on your knees sucking their
big hard cocks."

"Oh god." He moaned as I stroked and kneaded his tight round bottom.

"Time to pull your panties down." I whispered, feeling him tense. "Just
relax, Jack. If you behave I won't spank you hard at all tonight."

"Oooo."

"Say thank you Daddy."

"Ohhh... thank you Daddy." He sobbed softly as I slowly worked the pink
panties down over his ass. This time I took them all the way off and spread
his legs open wide.

"Keep your legs open, Jack."

"Y...yes, sir.... Arrrrr." He squealed as I spanked his bare bottom with my
hand.

"Are you going to behave yourself tonight, Jack?"

"Y...yes, sir. I will, I will... Arrr." He whimpered as my hand landed
again on the other cheek.

"You're a good little sissy boy now, aren't you Jack."



Yes Daddy."

"Say it."

"I'm a good little sissy boy for my Daddy."

Pushing him to the carpet between my legs, I stood and dropped my shorts,
kicking them aside as I took his head in my hands. He let out a sob as I
pushed the tip against his lips and he obediently opened his mouth so the
head could slip inside.

"That's a good little sissy boy. You know what you are supposed to do now,
don't you." Jack nodded and started sucking my cock as I pumped it in and
out of his warm, wet mouth, his hands holding onto my thighs, but he wasn't
crying enough for me yet.

"What a dirty little pervert you are, on your knees with a man's hard cock
in your mouth." Jack sobbed and he started crying.

"Yeah, what real man would every do something as dirty as this." More
tears. "The only thing sissy little Jackie is good for now is sucking men's
cock like a dirty little faggot." That broke the damn and he sobbed around
my cock as I pushed it deeper into his mouth. This was what he wanted, he
needed me to force him to suck cock, hating it and craving it at the same
time. He couldn't willingly admit he wanted to suck a cock as that way he
could always tell himself that he'd been forced to do it against his will,
thereby preserving the illusion that he was still a real man. The faster I
pumped my hard cock in and out of his mouth, the harder he gripped my
thighs. I smiled and let go of his head to see what he'd do, but he didn't
pull back and take the cock out of his mouth. He pushed his head forward as
I thrust inside and down his throat, barely making him gag at all. I took
his head again and forced my cock all the way in to the balls and held it
there, just to see how long he could hold it. It was much longer than I
thought before he pulled back and gasped for breath, looking up at me with
pleading eyes. Pleading for what I wasn't sure so I slipped my cock back in
and fucked his mouth. I had to stop as I didn't want to cum in his mouth
tonight, wanting to save a big load of cum for when I fucked his virgin
ass. Jack looked a little disappointed when I pulled out and patted him on
the head.

"That's a good sissy. You did well tonight. Put your panties back on and go
get yourself a drink. Slowly he did, occasionally glancing up at me,
blushing slightly. When he return I dropped a pillow on the floor beside
the couch and he obediently sat on it. Relaxing, I switched on the TV and
we watched a movie together and it wasn't long before Jack was leaning
against my leg with his hand on my thigh. I guess he was a happy little
camper tonight.

The week went by much the same, with me `forcing' him to wear his panties,
bra, stocking and garter belt to work each day. I'd always inspect him in
the morning, adjusting his slutty lingerie to my liking and patting his
bottom as he ran off to finish getting dressed. He did tend to swish more
as he walked about the office and he was more prone to crying a little if I
said a harsh word to him or give him a stern look of disapproval at
something he did. He also got use to swishing around the house in his
slutty lingerie and not blushing so much when he caught me watching him.

"Have you ever been to a spa, Jack, or had a facial?" I asked casually one
Friday evening.

"No, sir I never have. My mother used to go to the spa 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 spa 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, Daddy, when?"

"We'll go tomorrow morning at eight. Just wear a pair of short, a tee
shirt, and sneakers, clear?"

"Y...yes, sir." He answered, looking puzzled.

"I promise you'll feel like a different person coming out than the one you
did going in." I said, adding a small laugh. Jack looked at me a little
uncertainly, but smiled and blushed.



END PART TWO