The Making of sissy Jizzelle

Matt was in a dead end job, he'd been looking for something new for months when he came across a posting for a new position. He applied, interviewed and hired in no time at all given his superior qualifications. Things were going great and he fit it with everyone at his new place of employment. This new job was almost too easy for him. Matt found that he had a lot more free time and his thoughts often turned to sex. He would watch videos, secretly listening with his ear buds on his phone or read stories in the mornings and masturbate at lunch in his office almost every day.

Matt was married to a beautiful woman but the marriage was sexless for more years than he could remember. The lack of sex somehow fueled him to explore more taboo themed porn. Maybe because he felt guilty and responsible for the no sex part of their relationship. One day he watched a video about chastity that also hinted at forced bi. He found when he watched those videos he had more powerful orgasms.

He was always looking for something new to jerk off to and accidentally came across a video about being "pussy free," he quickly blew his load after the first few minutes of watching it. He watched and jerked to the same video the rest of the week. Each time he came with more intensity than before.

By the end of the week he made it to the end of the video but noticed the last two minutes of the video were especially arousing. Messages flashed on his screen. Subliminal messages that flashed on the screen that only sissies should be pussy free.

Weeks passed as Matt became more and more interested in watching these new videos over standard porn. He let himself slip into a trap and gravitated toward forced bi, sissy Hypnos and chastity. Each time he jerked off to those the guilty feeling after was less. After six months he found himself purchasing a chastity device to try.

He bought several, wore them for a while then took it off to jerk his cock. He found that the more accommodating devices actually caused more pain since they let his cock get a little bit harder. He finally settled on a pink nub Holy Trainer version 4 that was comfortable enough to wear all day.

Matt would watch porn while wearing his pink nub and then at some point remove it and jerk off. It became a routine.

Eventually he started watching more taboo videos and he found the ones that were sissy themed really excited him. His curiosity turned to obsession and soon Matt was fixated on porn that had an interracial flair. One day he came across a Hypno called BBC Worship for Sissies and Cuckolds volume 2. It was a turning point. Something in the videos released his inner desire to become a sissy.

Over the next several months Matt purchased several sissy outfits online and had them sent to a drop box near his home. He kept them at work in a locker in his private office. He would get to work early and put an outfit on and jerk his cock to sissy porn. It was now implanted so deep in him he started dreaming of it at night.

One of the overarching themes in his jerk off themes was that sissies should suck cock and submit to Alpha males. Being pussy free for so many years made it easy to fantasize about cocks instead of pussy since he was not getting either.

His jerk off sessions were getting more complex and involved than ever before. He would dress up in panties and stockings, pop a butt plug in his ass and jerk off, wishing for more each time.

Then, one day he watched a video that suggested he post a listing on an adult sex site and find a cock to suck.

Matt had never posted an ad before but the thought of it intrigued him, thinking of sucking cock had been on his mind for a long time now, especially with the help from the videos he'd been watching and jerking off to. So, one day he got up the nerve to open up an account on an adult app that was for gay guys.

Matt got on the app every day to check for potential hookups but always chickened out until one day, in the heat of a chat with someone, he accidentally gave out his cell phone number.

Almost immediately he got a text from someone. The text read:

"Does your wife know you're a cocksucker?

I know who you are now, if you want to keep your secret safe you will do what I say, or else."

Matt was scared. He'd sent pics of himself dressed up in panties and short skirts with his chastity cage on and was afraid he might get outed to his wife or someone else. He decided to play along just to be safe.

Matt replied that his wife didn't know anything and he was willing to do what it takes to remain a secret. There was no reply.

Matt didn't sleep well that night, dreams of sucking cock and being paraded around dressed in skimpy outfits filled his head. He woke with a raging hard-on.

Later that day at work Matt got another text that gave him an address with instructions to be there at 4:30 that afternoon or his pictures would be sent to his wife's cell phone. Matt's heart skipped some beats and the anxiety and fear crept in quickly. Although part of him was scared shitless another wanted nothing more than to follow through with the instructions.

After work, Matt drove to the address and parked on the street. He was early so he decided to wait in his car. After a few minutes someone approached and tapped on the passenger door. Matt powered down the window and the guy immediately introduced himself as Richard, the guy he met online, and asked if he could get in the car to talk.

Matt unlocked the door and let him in.

There was an initial moment of silence before the man spoke.

"I'm glad you decided to come, would have been bad for your wife to see those pics of you dressed like that you know."

Matt nodded in response and said, "I agree."

Richard asked Matt to drive. "I'll give you directions as we go," he said.

Matt drove, not knowing where they were going. They eventually arrived at a house in a very up scale neighborhood.

Richard pulled out a door opener from his pocket and used it to open one of the doors on the 6 car garage. Once in the door closed and Matt turned off the car.

Richard told him to get out of the car and follow him.

Matt walked behind him though a door and into the house.

It was a very nice home with great ocean views. Matt followed him and they stopped in a large seating area. Reminded Matt of a hotel lobby.

Richard sat down and motioned for Matt to take a seat across from him.

Matt sat nervously as he watched Richard pick up a tablet and make some gestures before setting it back down.

"So, you're in a sexless marriage and you're looking to explore, am I right?" Richard asked.

Matt replied, "that about sums it up."

Richard snapped quickly, "from this moment on you will refer to me as Sir or Master, understood."

Matt quickly snapped into his submissive persona and replied, "yes Sir."

"Better bitch," Richard said.

Matt had been called a bitch before but the way Richard said it made it more derogatory than ever before. It felt shameful and that somehow actually excited him.

Richard started to explain the reason for all the caution and scare tactics was to ensure Matt was who he said he was and to sort out all the flakes he normally ran into when trying to hook up. He told Matt that he wouldn't do anything to jeopardize their privacy unless Matt did something first.

Matt was so relieved at hearing that he almost started to cry.

Richard and Matt spent the next 30 minutes talking and exploring each others fantasies. Matt told Richard all about his fetishes and how he got so caught up in them.

Richard didn't reveal much at all, he only listened and smiled reassuringly and asked leading questions. He concluded that Matt was a genuine sissy faggot iand he was going to enjoy this new relationship.

Matt couldn't help but notice a huge bulge in Richards pants, his eyes gave him away on several occasions when Richard caught him staring.

Matt blushed.

He learned Richard was married too and he and his wife had an open relationship that included same sex partners. His wife Sara travelled a lot for work and was hardly ever home.

Richard offered Matt a drink which he politely declined. "Politeness is an essential sissy trait, I'm glad to see it in you," Richard complimented. "Besides that, I think you're thirsty for something else aren't you?"

Matt looked at his watch. "Need to be somewhere?," Richard asked.

Matt stammered, "yes Sir, I should be home in an hour or my wife might ask questions."

"Then we should get down to business," he said as he stood up and pulled down his pants. Richard exposed a massive hard cock that bobbed and pointed directly at Matt.

Matt sat, his eyes fixed like a deer caught in the headlights of an oncoming car. The snap of Richards fingers brought him back.

Matt trembled and instinctively started to sink to his knees only to hear Richard say, "Sissy cocksuckers need to dress the part when performing their duties."

"Strip all your clothes off and put these on." Richard reached under a pillow on the sofa and pulled out some skimpy lingerie and tossed it.

Matt caught the lingerie, it felt like silk. He was nervous about stripping. He was still wearing his pink nub chastity and felt embarrassed by it, but managed to pushed through it.

The silky crotchless panties and short skirt slipped on easy but didn't begin to hide anything. They felt good next to his skin. He slipped into the lacy bra and adjusted it. He stood there, feeling intimidated and insecure waiting for Richard to make the next move.

Richard stood up and circled Matt. The skirt was so short it didn't even cover his chastity. He felt Richard's hand brush up against his ass.

Richard noticed precum was beginning to leak from Matts cage and smiled. He touched it and got some on his finger and brought it to Matt's lips. Matt obediently opened and tasted it from his finger.

The taste lingered.

Richard pressed two then three fingers in Matt's mouth and pressed his tongue in the back causing him to gag. Waves of humiliation hit Matt hard. Richard removed his fingers and stepped back.

"That's much better, "Richard said, "I think you have the potential."

"Now, I'm going to explain a few things while you work, understand?" He continued.

Matt responded, "yes Master," feeling even more submissive dressed as he was.

Richard sat back down, he motioned Matt to get between his legs as he sat back on the sofa.

Matt crawled toward his cock, transfixed on its size and girth. At full erection Richard was easily 9 inches with a thick bulbous circumcised head and huge veins pulsing in its shaft. He was dripping with precum.

All the sissy Hypnos that Matt had watched up till now could not have fully prepared home for the real thing but thinking about them helped him focus on what he was about to do. Suck cock.

He leaned in and kissed the top of Richards cock. "May I please suck your cock Master?," Matt said submissively.

He looked up into Richards eyes and remembered one of his sissy Hypnos. "Sissies keep eye contact when sucking superior cock," the voice in the video commanded. "Sissy faggots must always show proper respect when in the presence of a superior Alpha male."

The voice repeated in Matt's head. It had become his internal voice when jerking off over the last several months conditioning him for this very moment.

Richard reached down with both hands and pulled Matt's head down onto his cock abruptly catching him off guard. Matt choked a bit with just a 3rd of Richards cock in.

The texture was amazing and smooth, nothing what he was expecting. Its girth stretched his lips. The smell was musky and manly and filled his nostrils creating an olfactory memory of Richards huge cock.

Richard started talking as he guided Matt's head up and down part of his shaft.

"First things first, you need a sissy name so there's no question what you are. The next time we meet you will have one, make sure it's good or I will give you one that may not like. Got it?," He paused waiting for a reply. Matt sensed this and nodded his head affirmatively while still sucking and keeping eye contact.

"Rule number 1," Richard said. "When in my presence you will be dressed appropriately at all times. What this means is, proper sissy attire. Panties, skirt, bra are a minimum. I have lots of sissy clothes for you here but I expect you will purchase more on your own. Surprise me with something sexy and you might be rewarded," Richard said.

Matt responded appropriately with a head nod and a muffled grunt around the cock lodged in his mouth.

He hadn't really noticed but he was gradually getting more and more of Richard in his mouth. It was beginning to enter his throat causing tears to form in the corners of his eyes. The tears eventually ran down his cheeks.

Richard continued talking. He explained to Matt what he demanded in return for allowing him to suck his cock.

Matt knelt between Richards legs, bobbing slowly up and down his thick shaft as he listened to him in disbelief. It seemed Richard was twisting things around to make it seem like it was a privilege to suck his cock.

Deep down he knew it was true, it was a privilege to suck Richards cock. It was the epitome of manliness and commanded respect.

Matt reached up with one hand and started stroking Richards cock, Richard slapped it away.

"You will find that I don't like hands on my cock, understand?," Richard said. "Keep them behind your back. If I'm fucking your face really hard you have permission to hold onto my ass to keep your balance. Understood?" Matt grunted an affirmative, still maintaining eye contact just like his sissy Hypnos had taught him.

Richard pushed deeper into Matt's throat, reached back to his exposed ass and gave very hard slap catching Matt off guard.

It stung and left a red hand print on Matt's ass cheek.

It was real now he thought and made a mental note not to touch it with his hands again.

While Matt sucked, Richard talked. It was hard to concentrate on listening and sucking at the same time.

"You have potential but you need some work. I'm willing to allow you to submit to me but only on my terms," Richard said.

"I'm going to allow you to suck my cock every day after work this week. If you can do that, and not miss a day, then I will consider letting this arrangement continue," Richard explained.

Distracted by the act of cock sucking, and being spoken to as if it was a privilege, was almost too much. His restrained cock tried in vain to get hard.

Precum oozed from the opening and long shiny strings dribbled out and swung back and forth as Matt bobbed his head on Richards shaft.

It was by far the most humiliating and exciting situation Matt had ever experienced. He was instantly hooked on Richard cock.

Richard looked at the clock and decided it was time to wrap things up. He started thrusting his hips up and pressed on Matt's head. He looked down. Matt was still maintaining eye contact. He hoped Matt was able to keep his part of the arrangement. He needed a cum bucket at his disposal.

Matt managed to take at least three quarters of Richard's cock each time he went down. As he sucked he thought of all he'd learned from his sissy Hypnos.

He used his tongue on the underside of the shaft, secretly wishing he was able to take his entire cock down his throat. He wanted to tongue Richards balls while his nose was pressed into his trimmed pubic hair. He was desperately trying to make him cum.

Richard was close. Matt could now taste the distinctive flavor of oozing precum from Richards cock. It was sweet, salty, and slimy which helped to lubricate this throat. He pressed harder into Richards crotch. Then it happened, Richards cock slipped past the resistance and into the back of Matt's throat.

It came unexpected. Suddenly, Richards cock was buried to the hilt in Matt's throat. He seized the moment and squeezed his tongue out under Richards shaft and swirled it all over his massive balls.

He maintained eye contact but everything was blurry from the tears that were flowing. He couldn't breathe but held his position. He wanted to make Richard cum. He wanted to experience what, up until now, had been a jerk off fantasy.

Richard grunted and growled, "take my load you sissy faggot." Matt tried to pull back but Richard held his head firmly. Seeing Matt struggle pushed Richard over the edge and he started cumming in Matt's throat.

Rope after rope of hot cum filled Matt's mouth and throat. He could breathe now through his nose but cum and snot bubbled out his nostrils with each breath. He had cum oozing out around his lips and Richards cock. He was in sissy heaven.

Richard pulled out and rubbed his dick all over Matt's face, adding to his humiliation. "Keep that cum on your face, I want it to dry there so you can think about it on your way home," he said.

Matt wanted so desperately to jerk off at that moment. He wanted to get the keys to his chastity, remove it, and jack off while the cum taste was still fresh. Instead he knelt there waiting for Richard to say something.

He thought Richard had read his mind when he asked if Matt had the keys to his chastity with him.

Matt replied, "yes Sir. They are in my pants pocket."

"Get them," Richard said.

Matt crawled over to his neatly folded clothes and retrieved the key. He thought about unlocking himself but instead crawled back over to Richard and held them up for him.

Richard took the keys and set them on a side table. Matt looked up puzzled.

"I'm going to hold these until tomorrow," he said to Matt. "It's to make sure you return. I think you have potential and feel you need proper motivation to follow through." He paused to let his words sink in.

"I'm expecting you here tomorrow at 4:30 promptly, you know what will happen if you fail to show," Richard said.

Matt, still kneeling with cum smeared all over his face replied, "yes Master."

"Now get dressed, but leave the cum on until you get home," Richard ordered.

"Keep those sissy clothes on under your street clothes too. I want you to immerse yourself in all things sissy." He paused, "you want that, don't you?," Richard asked.

Matt was so sexually aroused at that moment he would have agreed to anything. "Yes Master," was all he could think to say.

Matt dressed, keeping the silk girly bra, panties and skirt on under his clothes. Nothing was noticeable except for the dried cum on his face.

Richard led Matt to his car, opened the garage and watched as his new found sissy bitch drove away. He felt confident Matt would be back.

Matt drove, cursed himself for giving up the keys to his chastity and occasionally glanced in the rear view to see the cum dried on his face. He would have jacked off in a parking lot somewhere on the way home he was so horny.

When he got home, he realized his wife was not there yet. Then his phone buzzed and he looked. It was a text from Richard.

He opened the attachment and looked in horror and excitement to see it was short clip of him as he sucked Richard's cock. Richard had videoed their entire session.

Matt undressed and cleaned up wondering how he was going to keep his chastity device hidden from his wife. Not that they were having sex but they did use the same shower and dressing area.

He decided it would be best if he showered early the next morning, before she got up, to keep his pink nub a secret.

Matt slept well that night except for the half dozen times his caged cock tried in vain to get erect and woke him. Every time he fell back asleep he dreamed of sucking Richards cock. It seemed like an endless cycle.

When he woke the next morning he quickly showered and slipped his sissy clothes on under his work clothes. He made some coffee, kissed his wife and left for work.

It was a busy day for him but 4:00pm came fast. If he hadn't been kept locked up he would have jerked off 2 or 3 times after his meeting with Richard yesterday. The cage kept him constantly aroused and unable to cum.