The Making of sissy Jizzelle

On the drive to Richards house he wondered what he had planned. Once in the driveway he noticed the garage open and Richard standing there motioning him to enter. He did.

Richard closed the garage door and Matt got out of the car.

Richard smiled and instructed him to strip and put his clothes back in his car. He did and stood there, dressed in his sissy clothes and pick cock cage. He was dripping with excitement.

"Glad you made the right choice sissy bitch," Richard said.

"Me too," Matt replied.

"Come with me," Richard ordered.

Matt followed. They walked in and went down a long wide hallway, with expensive artwork on the walls, to a dimly lit room.

There was a round bed with rubber sheets and leather handcuffs in the middle of the room.

On the walls were sets of bondage gear and whips. Matt had no idea of what some of the things were.

Near a small table with shackles was a Sybian with a dildo attached. Matt recognized it. It was similar to one in the videos he liked to watch where a woman ( Matt always imagined being the girl) was bound by hands and legs on a Sybian.

A harness was strapped on her head that held a huge ring gag. The back of the harness was attached by a rod to a motor.

The machine forced her head back and forth with such power she couldn't stop it.

In the video, a man stands over her, positions his cock in the ring and turns on the machine. Her head is forced repeatedly on his cock as he adjusts the speed of the blowjob.

The video finishes with him dumping a huge load in her mouth. The man leaves here there quivering from cumming multiple times.

Matt must have drifted but Richards voice made him turn away from the Sybian.

"So what is your sissy name bitch?," Richard asked.

Matt had forgot and his look said it all.

"I warned you," Richard said.

"I'm sorry Master, I forgot," Matt replied.

"Too bad cunt, I warned you, now... let me think," Richard paused for effect then said loud and clear, "Your sissy name is Jizzell Cockbreath."

"Like it?," Richard asked.

Matt could only reply, "Yes Master."

"Good, it suits you well," Richard said.

Richard went to a small dresser and pulled out a latex maids uniform, complete with apron and hat. "Take those off and put this on Jizzell Cockbreath," he barked.

Matt quickly stripped and started slipping into the latex. It was a totally different feeling from the silk. It stuck a bit to his skin, but he got it on easily, except for the zipper in the back. Richard saw, stepped behind him and pulled the zipper up.

Still behind him he ordered Matt to open his mouth which Matt immediately did.

Richard pulled a ring gag from his pocket and put the ring part in Matt's mouth, pulled it snug and buckled it. Matt was wearing a ring gag for the very first time.

Richard went to the dresser and returned with a pair of large silicone breast forms. He slid them into two zippered pockets on the front of the uniform, zipped them up and adjusted them. He stood back to admire his handy work.

Matt could feel drool forming in his mouth and tried to catch with his tongue without success. It dribbled down on his newly configured breasts.

Richard ordered Matt onto the rubber sheet bed in the middle of the room.

"On your back Jizzell," he said enjoying the sissy name he gave Matt even more.

Matt could feel the weight of the fake boobs on his chest. He always wondered how women with huge tits felt. Now he knew.

Matt laid on his back as he was instructed and moved his head to the edge of the bed. Richard pulled straps up and secured his feet and hands spread eagle.

He reached under Matt's arms and pulled him closer to the edge of the bed so that his head was leaning back over it.

Matt was totally helpless now and started to worry he was in too deep. He tried to chase any fear he had from his mind by thinking about his sissy videos he'd been watching.

Richard pressed a button on the side of the bed and it started to raise up. When it was level with his crotch he stopped.

Matt suddenly realized what was happening, as Richard unzipped his pants, Matt let out a little helpless whimper.

Richard entered Matt's throat with one quick thrust. Matt's view was blinded by Richards huge ball sack. He was definitely in way over his head.

Matt struggled, gagged and coughed as Richard assaulted his ring gagged mouth. Spit and precum dripped into his nostrils. Richards scrotum pressed against his nose cutting off air every time he bottomed out in Jizzell's open throat.

Matt struggled to maintain and soon figured out the timing of the thrusts. He was able to take small sips of air around Richards cock when he withdraw and left just the head in Matt's mouth.

"Fucking faggot. Take my cock you sissy bitch. Suck it proper if you want your reward, fucking cunt, suck it Jizzell," Richard yelled.

He pumped his huge meat in and out of Matt's mouth, he loved the view of his throat bulging out when he was balls deep.

He used his mouth like a pussy. Seeing Matt, now Jizzell Cockbreath, dressed up in the maids uniform with the fake tits made his cock swell. He was already close to cumming.

Matt was blinded, he could only focus on breathing. Everything else was secondary. He was not interested in his own pleasure, he focused on Richards cock, hoping to get him to cum so that he could breathe normal again.

Matt worked his tongue on Richards shaft. He sucked with his throat and it made gurgling sounds.

Hearing him struggle was all Richard needed to push him over the edge. He dumped a huge load in Matt's throat as he let out a loud, long groan.

Matt was grateful the assault on his throat was coming to an end. He didn't know how much longer he could have lasted.

Richard pulled out, and with a shudder stepped back. Matt could barely make out his silhouette through the stinging and burning cum that had dripped into his eyes.

Richard undid his restraints but left the ring gag in place. Matt sat on the bed in disbelief of what just happened.

Richard gave him a few minutes to catch his breath.

"Get your sissy faggot ass over to the Sybian now bitch," he yelled, catching Matt by surprise.

Matt, startled by the sudden outburst hurried over to where it was and waited, unsure of what to do next he turned toward Richard.

Richard grabbed some lube from a table and told Matt to hold out his hand. Matt complied and Richard squirted a good amount in his palm.

"Lube that sissy ass you fucking bitch. When you're good and slippery start working your fucking cunt down on that cock," he said pointing at the dildo on the Sybian.

Matt had played with his ass before with dildos so it wasn't new, but doing it in front of someone was a first. The waves of humiliation were returning. He knew it was too late to run, he was becoming Richards sissy.

He lubed his ass good, knelt over the Sybian and worked the tip of the cock into his ass. After a few minutes he had the dildo buried all the way up his sissy fuck hole.

Richard grabbed Matt's arms and bound them behind his back. He secured Matt's ankles to rings attached to the Sybian. Matt was now completely helpless for the second time that day.

Richard explained that the only proper way for sissy faggot bitches to cum was from anal stimulation. He told Matt that the only way he was going to be freed is if he had a sissygasm.

Matt remembered watching videos of sissy's having orgasms from anal. He had even seen them cum from anal in chastity, but never tried it himself. Today it was happening.

Richard pressed a remote and the dildo sprang to life. It vibrated and gyrated deep in his ass. It rhythmically bumped against his prostate causing him to dribble uncontrollably from his pink nub.

His mouth was still gapped open from the ring gag and the smell of cum overwhelmed his senses. Richard turned up the intensity and watched Jizzelle struggle.

After about 10 minutes Matt felt it. Warm sensations filled his belly and travelled to his pelvis. His ass was squeezing hard on the dildo and then it happened.

Matt's limp cock twitched in its cage. His balls tightened and he let out a loud grunting moan. Cum oozed from the tip of his pink cage and onto the padding of the Sybian. Matt just had his first sissygasm.

"Well that was pathetic," Richard said.

"You call that an orgasm?, I've seen women squirt harder than that. No wonder your wife doesn't have sex with you," he laughed.

Matt gasped, the dildo still moving in his ass coaxing the last dribbles of cum from his balls.

Richard stepped in front of him and put his cock through the ring. Matt looked up keeping eye contact with Richard. He squirmed a bit and pleaded with his eyes to be let loose. Richard looked down and started talking.

"Did you enjoy being defiled cunt?"

Matt batted his eyelashes to signal affirmative.

"Do you think you deserve my cock and cum bitch?"

Matt only grunted not knowing what else he could do.

"Well you have 3 more days to prove your devotion to me bitch," Richard said.

"Tomorrow I want you to call in sick and report here no later than 8am," he instructed.

"Come hungry because I'm going to give you plenty to eat," he laughed, as he pulled his cock out of Matt's mouth.

Richard removed the restraints and unzipped the latex maids uniform. He told Matt to remove himself from the Sybian.

When Matt stood up he felt his ass still gapped wide from the dildo.

Richard removed his gag and pointed to the mess of cum Matt left on the Sybian. "Lick it up faggot," is all he said.

Matt complied, reluctant but fearful of the power Richard had over him.

When he finished, Richard pointed to a door, told Matt there was a shower in there and to get cleaned up.

"Leave the clothes in there, keep the cage on your clit and let yourself out through the garage. See you in the morning Jizzelle Cockbreath," Richard said as he disappeared into the main part of the house.

Matt, almost zombie like, walked to the bathroom. It was a locker room size shower with all the accommodations.

He removed his latex suit and carefully hung it up, started a shower and enjoyed the hot spray on his tense body. The shower gel smelled like ripe tangerines.

Matt dried with one of the soft towels and hung it carefully. He proceeded wearing only his pink nub chastity through the sex room, through a huge open lobby like area and into the garage.

The door was open. He got his clothes and put them on. He got in his car, backed out, and drove down the drive. Looking in his rear view he saw the garage door close.

Matt could not sleep that night. He could not stop thinking about what happened. His cock strained in its cage at every thought that entered his mind. He had cum like a true sissy faggot... locked in chastity, a cock up his ass and cum down his throat.

Matt was living out his Hypno sex fantasies and it was an incredible feeling. Despite having cum earlier that day, while locked in his chastity, he was still horny as fuck.

Sometime during the night he woke up, his cock straining in its cage. He desperately needed to cum or he would never be able to sleep.

He reached down to his chastity cage and found that he could slip his pinky finger between the ring and nub and rub his flaccid penis.

After a few minutes he felt a warm feeling coursing through his balls. He rubbed faster. He fantasized and imagined he was fingering his clit.

That was all he needed to send him over the edge. Cum oozed from his nub for the second time that day. He fell fast asleep in a sexually satisfying bliss.

Matt sent a text to his boss saying he was taking the day off. He dressed as normal but while in walk in closet he snuck a sexy lingerie outfit from one of his wife's drawers. "She'll never miss it," he thought as he stuffed it in his bag.

He arrived at Richards house and parked in the garage. His phone immediately pinged a text from Richard. It said for him to strip and come into the house.

Matt got out of his car and took his clothes off. He took his wife's lingerie from his bag and put it on. The outfit consisted of thong type panties that did nothing to cover his pick nub chastity, and a bra that had cut outs for the nipples.

When Matt entered the house he was greeted by Richard saying, "well, well, what do we have here?"

Matt sheepishly answered, "I was hoping to surprise you by putting on something sexy Sir."

"Something sexy is kinda pushing it Jizzelle, but not bad for a newby faggot bitch," he replied.

Richard motioned for Matt to come closer.

"Dance for me and show me what a slut you are for cock," he said.

Matt stood before him and gyrated his hips seductively and spun around a few times, he tried to do a twerking dance with his hips then Richard stopped him.

"Ok cunt, we will work on your twerk later, let's talk," he said and told Matt to kneel at his feet.

Matt scurried over and got on his knees. He felt nervous and humiliated that he just acted like a slut in front of Richard.

"Tell me how your night was bitch, did you sleep ok? How was that little clit of yours after yesterday?," Richard asked.

Matt confessed about rubbing his cock through the bottom of the cage and cumming again last night. This seemed to anger Richard a bit.

Matt regretted saying anything.

"Well we are going to have to ensure that never happens again," Richard said firmly.

"Chastity is meant to prevent you from touching your cock, or clit in your case, and I have just the thing to remedy that."

Richard continued, "Follow me Jizzelle."

Richard walked back into the sex room and Matt followed. Richard took the key to Matt's pink nub and unlocked it. Matts cock sprang to attention. His was a small penis by most standards but grew more that Richard expected from such a small cage.

Richard grabbed something from a small box on a table and told Matt to put his hands behind his back and keep them there.

Matt complied.

Richard removed a metal chastity device from the box. He reached down, grabbed Matt's balls and squeezed them hard making Matt wince in discomfort.

Richard slipped Matt's balls into the ring one at a time, then pushed his dripping penis thought as well.

He held up the cage part for Matt to view and explained how the device worked.

It had a long clear tube attached to a solid stainless steel piece in the back, it was completely flat in the front.

Richard explained that it was a negative chastity device and it would prevent a reoccurrence of the "accidental masturbation" Matt had last night.

He held the tube to Matt's mouth and said, "better get it nice and lubed because it's going to be in your tiny piss hole for a few days."

Matt cringed at the thought but stuck out his tongue and smeared spit on the entire 10 inches of the tube. He was scared as he had never had something poked up his urethra.

Richard pulled it from his mouth when he was satisfied with the lube job and the humiliation of his new sissy bitch.

He reached for Matt's penis and with 2 fingers held the tip still as he slid the tube into Matt's slit.

Matt felt a slight burning sensation at first but when Richard started fucking his piss slit with the tube, he felt the overwhelming urge to urinate, but nothing came out.

Richard watched with pleasure as Matt squirmed from the new uncomfortable sensations.

Richard pushed it deeper. The tube and the inverted part of the chastity pressed Matt's now flaccid penis back through the ring and folded into itself. It caused his cock to completely disappear. The tube completely negated any chance of touching his penis.

Richard used a special wrench to screw in a bolt that tightened the cage completely flat. Then inserted a lock and clicked it shut.

Matt's penis had completely disappeared. The sensations of being so confined with a tube pushed up so far caused him to whimper slightly.

Richard attached a small belt strap to one side of the ring and pulled it around his waist. He attached the other end to the cage and tightened it.

The belt kept the ring pulled tight against Matt and made the cage protrude more prominently.

Matt's balls were jutting out and up on full display but his cock was pushed back inside him, inverted and penetrated by the hidden tube.

Richard gave Matt a few minutes to adjust to the new device while he explained a few things.

"I don't like my sissy faggots jerking their clits without my permission, do you understand bitch?," Richard said forcefully.

"You will wear this negative chastity for the rest of the week to ensure you comply," Richard instructed.

"In the future I expect you will not play with your sissy clit without permission, in chastity or not, understand cunt," Richard stated more than asked.

Matt's sissy Hypnos had implanted suggestions that made him go completely into submissive sissy mode when he was called names. It was working.

As Richard talked Matt drifted a bit and started thinking of one of his Hypnos. It was one in which a beautiful mistress coerced the listener into only being able to cum for big black cocks. To only jerk to watching big black cocks fucking tiny pink holes. Matt started to leak precum from the opening of his flat cage.

Richard noticed and grabbed Matt by the face and held it. "Where the fuck are you?," he asked.

Matt, afraid to confess and even more afraid to hide, reluctantly told Richard about the Hypno he was thinking of.

Richard knew about Matt's Hypno fetish, they chatted about it online before they met. Richard planned to use it against Matt at some point to break him down further, to humiliate and expose his vulnerabilities.

"We have a long day ahead slut," Richard said. "Come with me."

Matt followed behind Richard. They went through a door and into a huge walk in dressing room filled with every sexy outfit Matt could imagine.

"Today you get to choose your outfit, just make sure it has room for these."

Richard held up two very impressive fake breasts. They had to be at least DDD cup size.

Richard pulled a razor from a drawer and quickly shaved the few hairs Matt had on his chest and underarms. He applied some glue to the breast forms and his chest, waited a few minutes and the pressed them into place.

Matt could not believe how heavy they felt. They pulled him forward and he found himself leaning back to keep balanced. This caused them to push out further. He looked down and the fake tits blocked his view of his protruding balls.

Richard opened another drawer and pulled out a platinum blonde wig. The high quality of it was easily noticeable. He put a hair net on Matt and positioned the wig and secured it in place.

"Now pick out something to wear and get dressed," Richard said before leaving, "I'll be back in a few to check your progress."

Matt could not believe this was really happening. He stood in awe looking at all the outfits for a second then started the process of selecting one.

There were skimpy panties, silk stockings, garters, pantsuits and latex everything including several styles if nurses uniforms.

Matt settled on a cute plaid school girls outfit. It was complete with white stockings and an ultra short skirt. The panties were crotchless and the bra barely contained his huge fake breasts.

He slipped it all on and adjust himself in the mirror. He looked like a slutty school girl except for the shiny flat cage and protruding ball sac that pushed through the opening in the panties. The skirt did nothing to hide his predicament.

He found some medium sized heels and tried them on. He walked around to get used to them and decided to try on some taller ones. They were awkward but felt comfortable on his feet so he decided to give them a go. He was enjoying every moment of his sissification.

Matt was finished and was admiring himself in the mirror when he heard voices. He felt a surge of adrenaline and trembled nervously wondering whose voices he heard.