Slow and Painful

Upon entering the locker room, Carolina threw Fred against a wooden bench, causing him to double over in pain. She then held the screaming and struggling boy down as she strapped him to the bench in such a way that his diapered ass stuck out in the air. She then pulled the diaper down, and set up a camera on a tripod in front of him before zooming it and focusing it in on his face.

In another unexpected show of inexplicable kindness, Carolina produced a water bottle and shoved it into Fred's mouth, giving him his first drink since his capture.

Despite the humiliating position he was forced to drink it in, Fred's throat had previously been burning with thirst, and the forced rehydration tasted better than any drink he had had before in his life.

Fred quickly realized however, that Carolina's kindness could only be the lead-up to something truly horrific. His fears were confirmed when she pulled a massive deep-purple strap-on from out of one of the lockers along with a pack of lube.

"This is a six incher." She said emotionlessly while spreading lube around his the edge of his hole.

"But we'll stretch you out to much much larger ones in no time."

Fred shuddered while she stimulated his rim, suddenly wanting more than anything to cum. As is if on cue, Carolina quickly produced another one of her awful rubber condoms, and slipped it on his half-mast dick.

As she compacted the bundle, Fred simultaneously gasped in pain and pleasure as his dick was crushed while a lubed covered thumb penetrated his butt.

"A few ground rules before I fuck you hard, rubber bitch." She said, with poison in her voice, "While my cock is attached you will call me Master instead of mistress. You may temporarily break no-no five only to call my strap-on a nice big cock. While you are being pegged, you will tell the camera how good it feels and how much you love master's nice big cock. Understand slut?"

"Yes Master Carolina."

"Now Fifi, what do you want me to do to you?"

Fred tried to steel himself as he prepared to sacrifice another part of his manhood, but he felt like a pathetic pussy. He had walked right into trap, over the past month he had squandered several chances to save himself, and now he was going to be penetrated by a massive strap-on cock and it was his own stupid fault. As the camera flipped on, Fred opened his mouth to answer:

"Master, Fifi Fuckpig's would love it if you filled its bum with your nice big cock. I want to be filled by you so badly."

"How badly Fifi?"

So so badly Master, Fifi loves your nice big cock so much and--- ahhh noooo owww."

Without warning the rubber dildo was violent shoved into Fred's asshole. He couldn't help but scream from a combination of shock and pain. He couldn't believe this was actually happening, he almost wished Carolina would hypnotize him again so he could at least think he enjoyed it.

As the strap went in and out of Fred's ass he got a stern reminder from Carolina:

"Talk to the camera Bitch! Let your fans know what's happening."

As he was violently pegged, Fred began speaking in between pants of pain and longing.

"Fifi's slutty bum is being stuffed tight by Master's nice big cock. Fifi loves the way that her kind Master is rewarding her for her good behavior. Although Fifi wants to make a cummie so badly, fuck-pigs aren't allowed to make cummies, even when there filled with a nice big cock."

As Fred spoke himself into humiliation, he felt Carolina shove the strap even deeper into his hole, and began grunting and moaning like a pig. Embarrassingly (if that word had any meaning to him anymore), he really did want to cum from having his ass fucked. The rubber prison held his cock nice and tight though, and the tortured sissy could only continue to grunt degrading sounds of pain:

"Oink! Oink! Master's cock is making Fifi feel like such a good rubber pig! Fifi hopes master will keep fucking it forever in its tight sissy bumhole!"

Carolina abruptly finished, shoving her cock all the way in so that her hips touched Fred's butt cheeks, and causing to Fred moan with a frustrated sexual longing.

After she removed the anal invader, Fred felt her shoved a small butt plug with an attached pump into his gaping cavity. She slowly began to inflate the pump until it was slightly wider than the strap-on that had just entered his ass, stretching him while making the possibility of removal without deflation next to none.

Using a hand mirror, Carolina gave Fred a nice view of the state of his recently fucked anus. His ring was stretched to the size of large coin, and Fred noted that the end of the plug which was sticking out was adorned with a pinkish spirally pig tail. The boy oinked with embarrassment.

"Fifi is going to be a great cheerleader one day."

Carolina stated this while running her finger across Fred's trembling body, and slowly switching off the camera. After this she continued speaking, while shaking her hips and waving the shit streaked strap-on in her slave's face. Fred wanted to wrinkle his nose, but the hook prevented that, so he breathed heavily through his mouth to avoid the stench.

"Now, my pet has to make a choice. In a few hours, Goddess Mindy will be home from classes. Because of your good performance at cheer practice, you have earned the removal of your sissy diaper."

"Thank you Master." Fred said, relieved.

The removal of the diaper was, unknowingly to Fred, an insidious part of his training. By making him believe that good behavior would actually cause the girls to show any significant mercy on him, Carolina was strongly reinforcing his submission.

The submission was furthered by the fact that the water he drank had been pumped full of tasteless females hormones and drugs that would keep the boy confused and weak. The hormones would also begin, along with the strict corset, to give him a more female figure and voice while preventing the return of his body hair.

"While you are waiting for Mindy you can either: use your mouth to suck your pissy diaper clean, Lick all of your shit from off of my cock, or choose neither. If you choose neither then Mindy will be informed of your choice."

Fred gulped, he knew Mindy was already mad at him, but he couldn't stand the thought of either piss or shit going into his mouth. Besides, he thought, that was probably pretty unhealthy, and he needed to keep his health if he wanted to escape. He was going to have to risk Mindy's wrath.

"Master Carolina, Fifi would like to do neither of those things please."

Carolina laughed her blood-curdling laugh as he left the room and switched off the lights:

"O God bimbo-boy, you really have no idea what a dumb fucking decision you just made."

Fred was left alone, shuddering with sexual frustration and securely tied to the bench, to ponder what horrible fate he had just signed himself up for.

...

After an indefinite amount of time in bondage and total darkness. Fred's frustrated and denied sexual frustration began to wear off. His body was wracked with the ever present pain and soreness of his restrictive outfit, extenuated by the days the physical exertions and his lack of food.

Carolina had given him another water bottle to drink from before she had departed, and Fred supposed he should be thankful for small favors.

He wanted desperately to escape, but despite all the signs around him he couldn't comprehend the idea that the girls were truly going to keep him here forever. Some hopelessly optimistic voice in the back of his head kept on telling him that if he played along well enough they would eventually get bored and let him go. Fred embraced that voice, as he was much to tired and crushed to try to think about escape.

As he lay their waiting for Mindy to return and torture him, the high school locker room triggered another kind of humiliation for the boy, reminding him of his terrible high school attempts at romance.

Fred was not a particularly ugly or stupid guy, but he had taken his first few rejections hard and retreated into a shell that even college could never really coax him out of. He thought back to those long years of desperately wishing for some female attention, and realizing with sinking dread that he had finally gotten his wish in a severely twisted form.

He sat that and pondered this endlessly, until finally the door swung open and the light flipped back on. Mindy walked slowly into Fred's field of vision wearing the same work out gear she had clad during his first session with her all those weeks ago.

"Triggering any memories, Piggely-Wiggely?" she asked while smirking, "I just spent three hours at our home gym, getting all sweaty and stinky for punishment time."

Goddam three hours, Fred thought. It seemed he really had lost any ability to judge time at all. It occurred to him with terror that if continued like this, the slowly growing photo album on his bed room wall would be his only real indicator of how much time had past.

Noting Mindy's expectant face, the boy began to speak in the dreadfully humiliating way that his goddess loved so much:

"Fifi hopes your workout was wonderful, Goddess Mindy. It is nice to see that you still have the energy left to punish your naughty sissy."

Mindy smiled with pleasure, as she began to loosen Fred's bonds, before flipping him so he was face up and retightening the ropes holding him down.

"Your punishment is going to be something very special today, Sissy-poo, you were a very naughty girl and as a result I think it is appropriate to show you a new kind of fun that we usually save for more experienced Sissys. In addition, Mistress Carolina told me how uncooperative you were helping clean up after she gave you such a wondiforous fucking, and so I think it is time to better explain what kind of hygienic standards we will be holding you to."

"Yes Goddess Mindy, thank you."

With that Mindy sat her round and pert ass down on Fred's chest, and bent her legs so that she could push her foot deep into its familiar position filling Fred's mouth.

The nose hook prevented Fred from closing his mouth entirely, and he had little choice but to coddle and suck at the putrid foot.

Mindy pressed her foot farther into Fred than she had during his first worship session, and her toes touched the back of his throat, almost triggering a gag reflex. Fred's tounge was forcibly pinned to the bottom of his mouth by the sole of Mindy's foot, drowning him in the thick and acrid taste of sweat and foot gunk.

While Mindy pumped her foot in out of the boys' mouth like he was some sort of kinky washing machine, she continued to explain his "special punishment."

"Earlier today, Carolina told me that she taught you how to love a Master's cock, and that you took to your faggification quite nicely. While Carolina sees you as a useless whore could never pleasure her, I thought it might be helpful to teach my slut-puppy the proper way to treat and love a goddess like me. Sound good?"

Fred couldn't nod with his posture collar secured so tightly to his head, and couldn't answer while his mouth was stuffed so severely, so he gave Mindy's foot an extra intense suck to indicate his agreement.

"Good, then lets step this up a notch kay kay?"

Mindy removed her foot from the boy's mouth, and pulled a round and bright pink ball gag out of a nearby locker. The gag was stuffed in Fred's straining mouth, before being buckled securely to the back of his head.

As the gagged filled and caressed his mouth, Fred suddenly was overwhelmed by a new and unexpected taste. It was sour and unpleasant and seemed to almost bubble around his mouth. Suds began to build up around the gag and-- Oh god, he thought when he realized what was going on.

Mindy smiled and then gave him her infamous perverted look of sympathy as she watched him struggle with the ball of soap she had just gagged his mouth with.

"Now slut-puppy, you must understand that sissy's are dirty sluts with gross unclean mouths, and before they worship their goddess they must be thoroughly cleaned. Being cleaned out with the soap gag may not be pleasant though, so lets do something to distract you!"

With this Mindy lowered her pants and panties, and turned around, presenting her lovely behind to the gagged and sputtering slave. She made like she was about to smother him, but stopped an inch above his face before adjusting herself so her butthole hung right above his nose.

Mindy's sweaty bare butt-cheeks rubbed against the cheeks of Fred's face but that wasn't the worst part. With the massive gag filling his mouth with soap, Fred was forced to breath through his nose and inhale the tangy scent of Mindy's butt hole.

"Inhale that lovely stink sissy! Soon you'll learn to love it just as much as you love cock in your ass!" Mindy cheered while bucking up and down painfully on his rubberized cock knob.

She paused briefly to return to her normal position before smiling as she unleashed a terrible new kind of torture on the butt-sniffing sissy.

"Hope you don't mind Fifi!" She said as if it was the funniest joke in the world. "But even girls have to get a little gross sometimes."

"pffftttttt."

"pfffffffffffffft."

The fart was what Fred would call a quiet but deadly blast, a joke he would never again find funny. The stink of the fart had no where to go but straight into Fred's stretched out pig nose, and the scent filled him completely and made him feel sicker and more demeaned than any of his previous tortures.

As Mindy let out a rapid fire string of follow-up farts, Fred silently tried to scream and beg through the ball gag, forced to deal simultaneously with two very different unpleasant sensations in his mouth and nose.

At first the slave began to furiously suck on the soapy ball, hoping to cancel out the sickening stench of the fart. When the strong and sour taste of soap became unbearable, he switched to deeply inhaling Mindy's tangy farts, but in not to long he was dizzy and nauseous from the overwhelming stink once again.

After repeating this switch back and forth five or six times, Fred felt close to vomiting. His constant sucking on the soap ball had finally shrunk it down significantly, and he took advantage of his soap filled mouths new freedom by screaming at the top of his longs.

"Pleeeasssse Goddess! Have mercy on Fifi!"

He hated this torture more than anything, it made him feel lower than even the strap-on fucking, and he was literally being transformed into a hygienic machine made to suck up his mistresses disgusting farts.

Mindy responded to Fred's pleas by smothering him completely with her bare ass, pushing the soap back into his mouth and forcing him to finished it while he suffocated under her behind. Once Mindy determined the soap gag was close enough to done, she unbuckled the remains of it and mercifully dismounted the screaming boy.

"So what did you think of that, my sweet little bondage toy?"

Remembering the first no no, Fred stopped trying to spit the foul taste he had just been filled with out of his mouth and replied miserably:

"Fifi is always happy to have it's mouth cleaned so it can better worship its owner, and Goddess Mindy's bumhole smells heavenly, especially when she fart right in to Fifi's piggy nose."

"That's great sissy-kins, its nice to know you liked being a fart-bitch, as its going to be a part of your daily schedule from now on! Now a question for you piggy-boy, do you think Goddess Mindy's dirty ass tastes as good as it smells?"

Before he had a chance to answer her dread-inspiring question, Mindy had already hopped back onto the bound sissy, this time placing her hole above his soap filled mouth, and declared:

"Tongue out sissy."

Fred didn't think he could do it, he just couldn't, so he sat there dumbly doing nothing until Mindy whacked him with an open hand in his balls and reiterated:

"Tongue out sissy! Or you'll smother quite terribly."

Fred wretchedly complied, and stretched out his tongue to begin to explore his mistress's butthole. A foul taste that felt like sniffing her farts times 1000 exploded into his mouth. Mindy cheered and moaned from the anal stimulation as she sat back down full weight on Fred's face, forcing his tongue even further up his butthole.

Fred could tell Mindy was extremely turned on by his rimjob efforts, and he felt her excited anal chamber begin to close around his tongue, trapping him in the disgusting butthole.

"Actually never mind bitch, I've just decided you're going to smother quite terribly anyways."

Fred's lungs screamed for air, as he furiously licked around and inside the vile butthole. He suddenly felt Mindy un-buckle his arm straps and heard her demand that he wave around his pom-hands in a celebration of the wonderful butt-worship session.

Without regular access to air (he was intermittently given small five seconds breathers from the smothering) this was an exhausting activity, and Fred earned several additional ball slaps in order to keep up his enthusiasm.

The punishment seemed to stretch on forever, and Fred began to realize why Mindy might be much more dangerous than Carolina. Carolina was smart and constantly aware, and seemed committed to causing just enough damage to motivate Fred without seriously or permanently injuring him.

Mindy seemed to have no such concerns, she was totally lost in the ecstasy of domination, and Fred could have easily smothered to death while her awful torture filled his mouth with the taste of ass. Even worse, Fred knew that if he wanted to make her happy, after the session was done he was going to spending a significant amount of time telling her how much "Fifi" loved being smothered while eating Mindy's butthole.

Mindy lifted off Fred's face to evaluate his performance.

"Your making a nice effort sissy, but I'm afraid that you must reach much deeper in order to fully clean out your Goddess's bumhole. In order to make it easier for you, I'm going to set up some extreme tongue therapy for my little bitch, so get excited!"

Fred was too lost and broken to answer, and was unsurprised when Mindy rewarded him for his silence with a rough slap to his face. After this, another gag was snapped into Fred's mouth, this one a dental device that held his mouth uncomfortably far open.

Mindy briefly disappeared, returning moments later and sticking her hand into his restrained mouth and grabbing his tongue to yank it painfully out from behind his lips. Fred suddenly felt a sharp and intense pain on the tip of his tongue, and Mindy used the hand mirror to show him that she had just pierced the end of his tongue and inserted a large powder blue metal ring.

"ankk ouuu" he stuttered with terror from behind the dental gag.

While Fred moaned, Mindy suddenly stood both of her feet on top of his chest, and grabbed a hook hanging from a pulley on the ceiling. She slipped the hook into his tongue ring before adjusting the pulley so his tongue was being painfully and intensely stretched, just below the point where the ring might have been torn out by the pressure.

Taking a tape measure to measure the extent of the stretch, Mindy sighed with dissatisfaction:

"Ugh you stupid fuck, we're going to need several inches added to that stretch before you can properly worship my bum. I think you'll be spending the night in here tonight, thinking about how you can be a better butt licker."

"ifi oo orrry" he tried to say, weeping. The stretch was truly intense, and Fred felt like his tongue was being pulled out from inside his mouth.

"Sorry won't help you, my poor little butt-sucking sissy, but I know what will."

Disappearing again, Mindy returned and began to add a row of three metal studs down the length of Fred's tortured tongue, causing him to wriggle hopelessly in pain. After she finished re-swabbing his aching piercings with disinfectant, re-securing his aching arms to the bench, and pouring another bottle of water into Fred's open mouth, Mindy looked at him and scratched her chin as she wondered aloud: