Bitch Boy

(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.