This story is Part 2 of Disciplining Derrick which is a spin off from the "Kimmy's Adventures" series. It is recommended you read part 1 first. The characters featured were introduced during "Kimmy's Adventures-Timmy's Virginity" and "Kimmy's Adventures- JUCO Recruit" which were published last year. The setting of this story takes place the following semester after the "Timmy's Adventures-College Tutor" and "Timmy's Adventures-Double D Debbie" tales which were recently published.
This is one of my darker stories in that it includes non-consent/reluctance, fem-dom, forced anal, and BDSM. There is also derogatory and homophobic language.
As always, this story is fictional and the product of my perverted mind. All characters depicted are over the age of 18. Any similarities to real people are a coincidence. It is told in the third person.
Derrick's Discipline Part 1 Synopsis
Derrick has just undergone phase one of his "behavior modification" for his overall callous behavior and specifically for the attempted molestation of a sorority pledge. While confined in chains, he was spanked repeatedly and brought to a ruined orgasm.
Derrick's Discipline Part 2
"Mistress, may Little Dick speak, please?" The dean nodded. "I've learned my lesson. May I please go now?"
"I'm afraid not my Pet," the dean replied, smiling wryly. "It is going to take a little more than a sore ass and balls along with a spoiled orgasm for you to truly change 20 plus years of learned poor behavior. The next two phases are designed to help reinforce the message."
With that said, Mistress Levy gave the signal for phase-two to begin. Suddenly a team of six girls broke into action like a well practiced NASCAR pit crew. One girl immediately appeared with a portable urinal allowing Derrick to relieve his bladder. Once he finished peeing, another sister appeared with a cup of water and a quick snack. Derrick drank and ate willingly, realizing just how thirsty and hungry he was.
After Derrick's personal needs were met, four girls loosened his arm restraints and slid a four foot long by three foot high bench behind him. Once the table was in place his leg restraints were unshackled from the floor. Before Derrick even thought of attempting to escape, he was lowered onto the furniture on his back and a seatbelt like strap was looped under the table and buckled around his mid section. Finally the spacer bar was removed from between his ankles then his wrist cuffs were attached to his ankle cuffs, essentially leaving him in a hog tied position, his butt plugged ass and cock fully exposed.
Showing she had some compassion, Mistress allowed for Derrick to have a cushion to support his back and prop up his head. The woman has an ulterior motive as she also wanted her pet to be able to clearly see what she had in store for him next.
"Ladies, please take your places," Mistress Levy directed the girls of Chi O. The sorority sisters quickly and quietly formed a semi circle in front of Derrick. "On the count of three ladies... 1...2...3!"
Derrick stared with trepidation as all at once the sisters of Chi O removed their cloaks revealing they were all similarly dressed in black lingerie with thigh high stockings. On their feet were four inch black heels that added to their intimidation. They all wore their greased hair pulled back in tight pony tails. Their make up was done in a dramatic gothic style with pale faces, lips painted purple, heavy eyeliner, and dark eye shadow. However, what scared him the most was the fact that every woman was wearing a leather harness with a menacing looking black dildo jutting from their crotches."
Derrick was about to protest but thought better of it. Instead he asked for permission to speak. Once granted consent he nervously and submissively asked what they had planned for him.
"Oh Pet, isn't it quite obvious?" Mistress Levy retorted condescendingly. "The girls are going to run an epic train on your cute, tight ass."
"Oh my god No!" Derrick screamed. "Mistress, please, No! I promise I'll change. I won't bother anyone....I...I'll even drop out of school,...you'll never hear from me again...but please don't do this!"
"Well, Pet, it's funny you should mention withdrawing from school, but we'll talk about that later, when the girls and I are through with you," the Dean said matter of factly. "But, No!. To just let you walk out of here right now would be too easy for you. I don't think you truly understand the pain your actions have caused to Shanon and others on this campus. So, as a result, Shanon and the girls would like to inflict some of their own mental, if not physical anguish on you first."
With that, Mistress Levy grabbed the base of the butt plug and yanked it harshly from Derrick's asshole. He yelled. Once again the women laughed at him as he laid vulnerably on his back, arms and legs bound in the air and his anus gaping widely.
Mistress Levy then picked up a bottle of lube and proceeded to pour a copious amount of the liquid into his wide open orifice.
"But, to show I'm not totally heartless, I'll help get your ass ready," the Dean said cheerfully. She then slowly began to work the index finger of her gloved right hand into his sphincter.
Derrick grunted audibly as he felt the digit stretch his asshole open again. He felt it slide back and forth several times before he sensed his mistress forcing another finger into his bung. Once he adjusted to the additional finger he felt the woman begin to work them in and out of his ass. The sisters of Chi O looked on intently. Derrick sensed his body betraying him.
"Look the fucking fagot is getting a hard on," one of the sorority girls yelled out derisively. Her fellow sisters laughed or chimed in with agreement.
"Now, now ladies," Mistress Levy chastised her pupils, "in fairness to Little Dick, the ass is an erogenous zone. If you rub a man's prostate you can provide him pleasure that will create an erection and even a very enjoyable ejaculation." The dean reached between Derrick's legs with her other hand and simultaneously stroked his cock till he was at full mast. "However, Shanon has...something... in store for you before we even consider allowing you to have any pleasure."
With that said, Mistress Levy removed her fingers from Derrick's ass. Then, he watched as Shanon, a buxom brunette, stepped in front of him, lined the head of the rubber dick up with his open asshole and gripped his thighs. She stared mournfully into his eyes. In one look he could sense the hurt and anger he'd caused to this poor girl that had been attracted to him the night of the party, but now detested him.
In one massive lunge Shanon thrust her hips forward, slamming the dildo deep into Derrick's bowls.
"Ahhhhhhhhuuuuugggghhhh!" Shanon screamed in release as months of rage vented from her body and was transferred to Derrick's ass through the dildo.
"Ahhhhhhhhuuuuuuuggghhhh!" Derrick screamed in anguish as he felt his rectum ripped open, despite the lubrication that the Dean had provided.
For nearly five minutes Shanon's grunts mingled with Derrick's groans as she continuously ravaged his rectum. While Shanon looked upon him cruelly, members of the sorority yelled words of encouragement to Shanon while other members spouted derogatory comments at Derrick.
Then, to Derrick's surprise, Shanon let go of his left leg with her right hand, reached between his legs and grasped his cock. The pain in his ass soon became pleasure in his dick as she stroked it in time to the thrusts of her driving hips.
Once again Derrick's selfishness got the better of him as he began thrusting his hips in time to the down strokes of Shanon's hand in hopes of cumming. He didn't understand he was playing right into the woman's trap.
