`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