Shopping And Sucking

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day.

He finished the sauce for the eggs Benedict got on his knees and waited.

He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between his legs.

It was a regular CB 6000s that was professionally modified and shortened to make more confining.

It was a constant reminder that his penis was not a source of pleasure anymore.

It was just a decoration of sorts, a focal point of his humiliation.

He knelt, waiting for his day to begin.

Debbie entered the room naked under a flowing silk robe.

Her breasts swayed with each step. She had no tan lines as she sunbathed exclusively in the nude.

A very handsome young man followed behind her completely naked, his huge cock bobbing and swinging semi-hard between his legs.

They both took seats at the table as Matt scurried to bring them coffee and finish preparing the eggs.

The lock on his chastity rattled as he moved causing Matt to flush with embarrassment.

Debbie and her stud Carlos made small talk and sipped the exquisite blended coffee ignoring Matt completely.

The two met at a museum charity event the night before.

Debbie seduced him and fucked him in one of the private offices there then brought him home and fucked several more times during the night.

Matt served them and went to the corner of the room, got on his knees and waited while they ate.

After a few minutes and without looking up from her plate, Debbie asked Matt, "how many cocks have you sucked this week?"

Matt replied, "fourteen Mistress."

Debbie snapped her fingers and pointed at Carlos. "Get over here and make it fifteen then bitch.

I want you to beg Carlos to let you suck his cock.

Convince him he should let you take a load of his cum down your throat.

Don't disappoint me cocksucker."

Hearing Debbie talk to him this way only humiliated Matt more.

Despite her verbal assault on his manliness, Matt's cock tried to swell inside the chastity device.

The tight confines of his "clitty cage," as Debbie called it, prevented Matt from getting anything that could remotely be considered an erection.

Matt crawled over to Carlos.

He looked up at his cock, it was huge and bobbed between his legs.

There was already a drop of precum at the tip.

"Sir, may I please have the honor of taking your cock in my mouth?"

He paused for a moment for a reply but got none so he continued.

"I promise that I'll be a good sissy bitch and give your cock the proper respect it deserves Sir. Please use my mouth and throat for your pleasure."

Carlos looked down at Matt and shook his head and chuckled.

He turned to Debbie and asked, "is he always this eager to suck cock?"

Debbie smiled, "he's always been a cocksucker deep inside but never had enough balls to follow through with it."

"I have to fight him for it now," she said matter of fact.

"He'd choose cock over my pussy right now... watch this."

Debbie turned and spread her legs wide open toward Matt exposing her nicely trimmed pussy to him.

Matt turned to look at her knowing what was about to happen.

"Pussy or Cock, its your choice," she said.

Matt turned back toward Carlos and begged to suck his cock.

"I don't deserve or want pussy ever again. I live to suck cock. My holes are just a place for real men to dump loads of cum," Matt pleaded.

"See, I told you," she said knowingly.

Carlos didn't know Debbie threatened Matt if he ever chose not to suck cock another 3 months would be added to his chastity.

If he sucked one a day would be taken off his chastity time.

Needless to say Matt was motivated to suck cock hoping he might get to use his penis again someday.

Debbie had other plans though. She loved to arouse and deny Matt of any normal sexual release.

Debbie tortured him with anal and prostate play.

She milked him regularly and allowed only an occasional ruined orgasm using a magic wand vibrator on his "clitty cage."

Matt was in a constant cycle of arousal and denial.

Carlos grabbed his cock and pointed it at Matts face, "come over here and get a taste."

Matt crawled closer to Carlos and put his face in his crotch, his lips brushed the tip of the cock.

Carlos told Matt, "put your arms behind your back and keep them away from my dick. Don't want your sissy faggot hands anywhere near my cock, you understand?"

"Yes Sir," Matt replied as he clasped his hands behind his back.

Debbie watched, her pussy was tingling with excitement. She reached down under the table and started rubbing herself.

"Open bitch," Carlos ordered.

Matt opened his mouth as wide as he could and remained still.

Carlos grabbed the back of Matt's head and pulled it forward.

With his other hand he guided his massive cock into his wide open mouth.

Matt's lips stretched to accommodate Carlos' penis. He curled them back over his teeth so that they wouldn't scrape.

Matt took a deep breath through his nose right as Carlos pushed down on his head.

Matt's eyes immediately began to water as his throat was filled with cock.

Carlos didn't stop pushing until the shaft was completely buried. He felt Matt's throat spasm and smiled at Debbie.

Matt struggled but managed to maintain his composure.

Debbie leaned close to Matt and said, "don't neglect his balls faggot... use that tongue and show them proper respect or you will regret it, believe me."

Matt managed to squeeze his tongue out from under Carlos' cock.

He flicked it back and forth over his balls.

Secretly he wished that he would have thought to do it before Debbie reminded him to earn her favor.

Carlos released his grip on Matt's head.

Matt took it as a sign to start sucking.

He was grateful to breathe again and slowly stroked the full length of Carlos' cock with his mouth and throat.

He pushed his nose against his trimmed pubes and held it there for a few seconds each time he leaned forward.

He pulled out just long enough to take a deep breath before pushing back down.

Matt continued bobbing and got into a nice rhythm.

He focused on giving a proper sloppy blowjob.

Debbie arched her head back and started cumming from fingering her pussy.

She loved watching Matt submit to her orders, the more humiliating it was for him the more it turned her on.

Carlos closed his eyes and leaned back to give Matt full unhindered access to his cock and balls.

Matt kept his eyes open and focused on Carlos. He watched his face react to the sucking and throating he was giving him.

He was truly worshipping Carlos' cock.

Debbie, finished her breakfast as Matt continued sucking.

With the shaft half buried in his mouth he managed to grunt out, "please Sir may I swallow your cum? I would be honored for the privilege of tasting your superior cum."

Hearing that made Debbie smile and soon afterward Carlos begin to spurt his load into Matt's mouth.

The sperm shot out like a canon as Matt pushed down on the cock.

Some of it squirted out of his nose.

He would be smelling sperm the rest of the day for sure now.

Matt swallowed, it wasn't like he had a choice. He lingered on Carlos' cock and licked it completely clean.

He took it back into his mouth and waited, the taste of fresh cum in his mouth.

Carlos eventually pulled his cock out and stood up.

Matt remained beneath him and said, "thank you Sir for allowing me to suck your superior cock and taste a real mans sperm."

Carlos ignored him, pulled Debbie up by the arm and said, "time for some real fucking now."

He took her to the master bedroom and closed the door.

Matt could hear them fucking loudly as he cleaned up the breakfast dishes.

The taste of cum was a constant reminder of what he just did. He had just sucked a cock while his wife watched him.

Matt finished then went to the bedroom door, kneeled and waited.

About an hour later Debbie called out for him to enter the room.

Entering on his knees he crawled over to the bed.

Debbie instructed him to clean up her pussy by snapping her fingers and pointing between her legs.

Matt quickly put his face in her crotch. He licked and sucked all of the sperm Carlos had pumped in her.

Once Debbie was satisfied she pushed Matts face toward Carlos' cock.

Matt licked it clean without question. As he did Carlos began to get hard again.

Matt wondered how could Carlos could have this kind of stamina. He'd cum at least a dozen times in less than 12 hours.

Carlos' cock grew rock hard once again as Matt licked it.

Matt's own confined cock and neglected balls were throbbing, full of cum and aching for release.

The effect of chastity on Matt was total obedience. He knew any chance of cumming depended on his submissiveness. He would do anything.

Carlos told Matt to suck his cock one more time and to make it good.

Matt obeyed and was once again deep throating and sucking cock like a good little whore.

Debbie watched her husband, always amazed how much it turned her on to see him as a sissy.

"Since she enjoys sucking your cock more than licking my pussy maybe I should make him a full time cocksucker. What do you think Carlos?"

"I think she gives a good blowjob but I'd rather be in your pussy," he said with a smile.

Debbie smiled back, "maybe she just needs more practice."

Carlos was close to shooting his load and said, "when I cum I want you to keep it all in your mouth but don't dare swallow a drop, got it faggot?"

Matt grunted affirmatively that he heard and understood his instructions and continued sucking.

Carlos' cock spasmed and filled Matts mouth full of sperm for the second time this morning.

Matt could hardly contain it all it was such a huge load.

He managed to slide Carlos out of his mouth without loosing a drop. He climbed off the bed got on his knees and waited for further instructions.

Debbie was actually impressed but chose to hide it. Instead she opened the bedside table and pulled out a head harness with a penis gag attached.

Matt dreaded being put in the penis gag. It was going to be even worse with his mouth full of cum.

Debbie held it up and Matt positioned his head and mouth to accept his fate.

The gag was wider and longer than most.

The first few times she used it on him he gagged constantly.

He was getting accustom to it now but it still could trigger his gag reflex if he didn't concentrate.

It was going to be even harder to focus wearing it with a mouth full of cum.

She pushed it in, tightened the strap and locked it in place.

Matts eyes widened with a look of fear.

Cum seeped around the gag but its length and girth prevented him from swallowing.

The sperm squished around in his mouth permeating every taste bud with the flavor of Carlos' ejaculate.

"There now, you can think about worshipping his cock all day long now," Debbie exclaimed.

"Go prepare a bath for me and then go to your sissy room and strap yourself onto the Sybian."

"I want you to use the big black dildo today and set the timer for 2 hours. I'll be in later to release you."

Matt crawled out and hurried to his room.

In the center of it was the fucking machine.

He went to the closet and got the big black dildo and attached it to the machine.

He lubed up and eased his ass down on the cock slowly.

He placed his feet and hands in the restraints that were attached to the machine.

He set the timer for two hours and then locked his last free arm.

He was now completely immobile and impaled on the fucking machine.

The machine buzzed to life and started its program. It randomly changed speeds and vibrating patterns.

It pushed against his prostate with each stroke causing him to leak from his chastity.

The penis gag pressed into the back of Matt's throat. The taste of cum lingered in his mouth. The dildo pumped relentlessly.

Thirty minutes later he felt it building deep inside him. He was going to cum from anal and there was nothing he could do about it.

His cock swelled and pressed against the chastity, he was on the edge of cumming when the machine stopped completely.

Matt was so frustratingly close that he began shaking and bouncing on the cock buried in his ass desperately trying to cum.

He screamed and moaned into his gag as he twerked on the Sybian. Finally the machine started back up again.

Matt shuddered and contorted, pulled on his restraints and then it happened.

Matts balls contracted and the cum that had been backed up inside him started to ooze out of his cock.

If Matt hadn't been in chastity he would have shot his load clear across the room.

Instead it barely escaped the tip of his sissy clit and dribbled out the hole in the chastity device.

As Matt struggled to recover from his ruined orgasm the fucking machine continued its assault on his ass and prostate.

Matt got fucked for another hour and a half on the Sybian. Twice he came close to having another ruined orgasm but was denied.

He was spent when the machine finally stopped.

The penis gag still coated with sticky sperm lodged in his mouth, his jaws ached.

Debbie walked into the room refreshed and dressed in a revealing low cut top and skirt.

"Has my little sissy faggot had enough cock yet?" she asked.

Matt shook his head to indicate that he still wanted more cock even though he really didn't. He knew Debbies little game all to well.

Debbie smiled down at him and said, "we will just have to get you some more cock then won't we?"

She released his penis gag and Matt swallowed the remainder of cum that coated his mouth.

She undid the restraints and told him to get cleaned up and dressed in the outfit she left on his bed.

Matt showered and applied hair remover over his body to keep it baby smooth.

He finished, went to get dressed and noticed what was left out for him to wear and felt a rush of anxiety when he saw it.

On his bed was a pair of pink frilly short shorts, a pale pink sheer top with the word "Sissy" in sequins across the chest and a pair of girly looking tennis shoes with ruffled socks.

He picked up the shorts to examine them and underneath was a large chrome anal plug adorned with a purple jewel.

Matt wasted no time getting dressed. If he wasn't ready quickly Debbie would certainly find a way to punish him.

He slid the anal plug in and slipped on the shorts. They were very tight and held the plug firmly in place.

The thin material of the shorts left an outline of his chastity device clearly visible, anyone that looked at his crotch would see he was wearing a cock cage.

He finished dressing and stared at himself in the mirror. He looked ridiculous in his pink outfit and felt a wave of shame and humiliation wash over him.

Matt knew Debbie had something up her sleeve but didn't have a clue what.

He found her waiting in the great room and he entered on his knees.

"Hello cocksucker," she said as he entered, "did you remember to take your pill this morning?"

Matt answered, "I forgot Mistress, I'll go take them now."

Debbie said, "I'm disappointed you didn't remember. Maybe if you take 2 of the blue pills today you won't forget to take them in the future."

"Yes Mistress," Matt replied, knowing not to argue with her.

Debbie made Matt take a Viagra everyday to add to his chastity humiliation.

His cock would be engorged and pressing into his small cage for hours. Taking 2 pills was sure to make it even worse today.

Matt took his pills and returned to Debbie who was waiting with her purse in hand.

She handed it to Matt and said, "be a dear and carry this for me today, we're going to the Mall to shop for some new outfits for you."

Matt cringed. Today was going to be difficult he thought as he followed her out to the car.

At the mall he followed behind Debbie carrying her purse.

He made every attempt to avoid eye contact with anyone staring at him.

The first stop was a piercing Kiosk where Debbie had the young girl pierce both of Matt's ears with 3 holes each.

They and fitted him with pink studs and large silver hoops.

The next stop was lingerie at a kinky Fredericks of Hollywood type of store.

Debbie selected numerous outfits, crotchless panties and bras then took Matt in the back to try them on.

She even brought one of the sales lady in the back to get their opinion.

Matt got a funny vibe from her but couldn't quite put a finger on it.

Karina was tall, she had a good inch on Matt. With her heels on she towered over him by a good five inches.

Her hair was black with a purple tint and her makeup was perfect.

Karina had a authoritarian look to her, a hint of masculine in her demeanor gave Matt an uneasy feeling.

Exposed to a total stranger was extremely humiliating for Matt.

He stood in front of them wearing his crotchless panties with his chastity poking out as they sized him up.

"Have you ever thought of putting him in breast forms?" Karina asked Debbie.

She held up a pretty lacy bra that matched his panties. "This is a DD cup... I think there is a nice set of nice silicone forms that are on sale that would fit perfectly."

Debbie asked her to go get them and took the bra from her hands to put on Matt.

She was adjusting the straps when the Karina returned with two boxes.

"Looks like the double D's are sold but I did find a pair of E and EE cups that might squeeze in ok," she said with a devilish smile as she took them out of the boxes.

Matt couldn't believe what he saw. The forms were huge and even had nipples poking out.

"Of course you'd want to use glue to keep them in place better but lets see what it does for her figure," referring to Matt as feminine.

She slid them into Matts bra and it made him blush with embarrassment.

The E cup fit almost perfectly giving him instant cleavage.

They examined them for a bit and had Matt jiggle up and down to see how they looked.

Karina pulled out the E cups and replaced them with the EE's. They were huge and heavy.

Debbie and Karina both smiled at each other. "I think we have a winner," Debbie said.

Karina said, "Maybe you should get him some implants. It would be a real game changer for him."

Debbie paused and thought for a moment, "I love that idea, maybe something bigger than these double E's will keep him focused."

Matt cringed at the though of having

breast implant surgery.

"I'll go get the glue," Karina said as she left the dressing room.

Matt started to speak but decided to just accept his fate.

Debbie and Karina spent the next few hours dressing Matt in the skimpiest outfits imaginable.

They agreed on several of them and left Matt wearing a short pink and purple mesh skirt.

His top was a thin pink knit sweater that pulled tight against his new EE breasts that were now firmly glued to his chest.

Everything about Matt screamed "slut" except for his face and hair. Debbie had plans for that later.

Karina and Debbie stepped out of the dressing room to talk.

Matt could hear them but couldn't make out the conversation.

It made him nervous.

When they stepped back in the both stared at Matt as if sizing him up for something.

After a few uneasy moments of silence Debbie approached Matt.

She put her hands to his face and looked in his eyes. "I'm going to leave you with Karina for a few hours while I go meet with Carlos.

You will do every thing she orders, understand?"

"Yes Mistress," Matt replied.

"I'll let you out of the store," Karina told Debbie as they walked away leaving Matt alone.