Cruel Tease - Chapter 4: Bring The Pain
Cruel Tease - Chapter 3: Abusive The Privilege
Cruel Tease - Chapter 2: Pain For The Sake Of Amusement
Cruel Tease - Chapter 1: A Poor Decision
Colin - a grad student who was silly enough to ask Linda to be his keyholder
Linda - a redheaded cocktease with a vicious dominant streak.
Erin - a sweet and innocent brunette college student. Colin is her TA.
Heather - a bratty and bitchy blond college student. Colin is also her TA.
The next week, Linda visited Colin again. She had left him in chastity for nine straight days - neglecting to return his calls and emails, preferring instead to leave him hanging. Finally, she called him and asked when he was available.
"Any day this week, except Wednesday, Linda. I've actually got a couple of things scheduled then."
"Oh, yeah? Like what?"
"I have my TA office hours from 3 to 4. And I have a couple of other meetings."
"Good. We'll meet Wednesday then. Reschedule your meetings, except for your office hours. I know that'll be inconvenient, but the theme of my visit will be 'Pain In The Ass', so that fits just fine. I'll be by at 1pm."
At 1pm on Wednesday, Linda knocked on Colin's door. "Open up, faggot!" she yelled as she pounded on Colin's door.
He hurried to let her in before the others in the grad dorm heard her. She stormed into his room wearing a tight pink sweater and short white skirt."I've had a lousy day so far... and I'm going to take it out on you. It's not fair, but too bad. Get naked and bend over the edge of the bed. I've got another 'present' from my shopping trip last week that I want to try out on you!"
Colin obeyed as Linda pulled a black leather paddle out of her backpack. Colin tried to move quickly, but he still noticed how incredible Linda's large breasts looked in the tight, fuzzy sweater she wore. Her white tennis skirt barely came down to her mid-thigh. Colin's swollen chaste balls began to ache as he put his elbows on his bed.
"Spread your legs more. And arch your back. I want a clear shot at your ass. Let's see how long it takes to make you cry with my new paddle." Linda held the new instrument of torture in front of Colin's face, so he could appreciate it up close. It was made of stiff leather. It was as long as her forearm and was five inches wide. The word "BITCH" was cut out of the black leather, so that the word could be read across the ass of the slave it was used on.
"There are lots of paddles like this. I had to choose from 'WHORE' and 'BITCH'... you're just lucky that 'COCKSUCKER' was too long to fit!" Linda pulled $60 out of Colin's wallet. "That should cover the cost of our new toy... Now, let's get to reddening your chaste ass up, shall we?"
Linda tortured the poor slave boy's ass for an hour and a half. Colin's face was streaked with tears when she finally stopped. His ass was a swollen red mess of crisscrossing welts and scratches. Linda had also used the paddle to rub Colin's sore ass cheeks raw in between brutal spanking sessions.
"Ha. It only took me five minutes to make you bawl like a little sissy with my new paddle. That's even less than I'd guessed. Maybe you are a little swishy sissy?"
Colin sobbed in response.
"Well, the next step in today's Pain In The Ass theme... let's plug up that slutty ass!"
Colin's eyes shot wide and he whimpered, "B-b-but...""'Butt' is exactly right!" Linda laughed as she jammed a large pink butt plug covered in lube into Colin's tight asshole. She slapped his abused ass just to make him jump. "Now, here's the fun part," she taunted him as she attached a hand pump to the plug. "I call this plug 'The Sissy Filler', because you can pump it up to enormous sizes. Watch, it'll get longer and thicker!"
Linda began quickly expanding the plug, doubling its size in just a few pumps. Colin began to sob.
"Oh, quit you're whining, it doesn't hurt that much." Linda laughed as she looked at Colin. "What? Did getting your asshole stuffed make your cock try and get hard? Are your balls all achey 'cause you like getting your ass filled up? Well, either way, you better get over it - because I'm not taking The Sissy Filler out or letting your out of chastity until tonight!"
Colin blinked back tears and tried to summon his resolve. It was difficult as his incredibly sore ass was radiating pain, his backed-up balls were aching terribly, his imprisoned cock was dripping pre-cum everywhere, and now his asshole was stretched to the max with the cruel pink buttplug.
"B-b-but, Mistress, I have to go to my office hours in just a little bit. I c-c-can't go like this!" he protested.
"Like hell you can't!" Linda shot back, smacking Colin in the balls with the "slut" paddle for talking back. "That's what I told you to do. So quit being such a little bitch and do it!"
Colin flinched. There were a number of reasons that he didn't want to wear his chastity belt and buttplug to his office hours. But the two more important were named Erin and Heather.
Erin was a student in the class in which Colin was the head TA. She was a fresh-faced brunette who was always bright-eyed and enthusiastic in class. She was a very average student, but tended to do well because her instructors could see her genuine interest in the subject matter. They could also see her large breasts, which Erin tended to accent with mostly unbuttoned dress shirts and flimsy midriff-baring halter tops. However, she had such a look of innocence about her, it was impossible to feel like she was knowingly manipulating men. But that was little consolation to male instructors when she leaned over their desk or bent over her work at the lab bench.
Heather was a student in the class in which Colin was the assistant TA. She was a striking blonde who acted like the TAs were lucky she had decided to come to class at all. She was very pretty, although she had a habit of wearing a bit too much make-up - especially for a lab section. Heather did well in most of her courses, especially those taught by men. She generally came to class dressed as if she was going to a dance club. Short skirts and backless, clingy tops were the usual for her. Heather would routinely walk into class looking like a rockstar with tight leather pants and revealing shirts with sections cut out and words like "Bitchy" and "Tease" splashed across the front. She was a very popular girl at the university, and it was clear that she knew exactly why that was.
Heather, Colin's blond college student
On the first day of class, Colin had immediately formed crushes on both Erin and Heather. He looked forward to teaching, and especially his office hours, because it meant he had a chance to interact with them. But Colin wasn't stupid, so he never mentioned his little obsession with the two co-eds to Linda. He didn't think his interest in them would go over well with his Mistress. And since Linda held the keys to his chastity belt, it made a lot of sense to keep her as happy as possible.
So Colin was now faced with the possibility of sitting through an hour of, at best, answering mundane questions while suffering through the pain of his spanking, chastity, and new buttplug. At worst, Heather or Erin might drop in - and then he would have to get through the conversation without giving away that this TA who thought they were cute was locked in a chastity belt with a pink buttplug shoved between recently spanked cheeks!
Linda quickly brought him back to reality. "What? Are you worried those sluttly little co-ed tarts are going to figure out that you're a cock-locked little pansy? Think the sorority girls will realize that you've got a red ass and a plugged asshole? You're not worried about being embarrassed, are you?" Linda giggled uncontrollably. "Because that's exactly why I'm making you do it! That's kinda the point of today's 'Pain In The Ass' theme! I'm sure you'll get through it fine, but I'm also sure it'll be pretty painful and embarrassing for you - and that's exactly what you need."
Colin quit sobbing and resigned himself to his fate. At least the pain shooting from his asscheeks had lessened to a dull ache. Now it matched the steady throbbing pain coming from his balls and asshole.
"Alright, it's almost time for you to leave. Let me help you get ready before you go." Linda dug around in her bag. She pulled out a pair of pink satin panties. "Here, put these on," she said with a laugh.
Colin stared dumbfounded at the panties. They had were covered in soft pink frills. His chaste cock and balls would be covered by a small pouch of clinging pink satin in the front. On the back, the satin was sown to bunch up the middle, emphasizing the curve of his very sore butt. The panties screamed, "Sissy"!
"Well, put them on and say thank you," Linda said impatiently. "I've got things to do, and you're going to be late!"
"T-t-thank you, Mistress," Colin said. His heart was obviously not in it.
"You're welcome. I picked these out because the satin won't breath, so you'll get hot and extra uncomfortable. Plus, I got a smaller size so they'll be really tight - that'll keep The Sissy Filler way up inside you where it belongs, and it'll crush your cock cage back into your swollen balls. And I think it's just your color, too, homo!"
Colin pulled them on and discovered that Linda was right about how uncomfortable his new panties were. He quickly pull on pants and realized just how painful the next few hours would be. He would have to move as little as possible, a difficult task if many students stopped by, to minimize his balls getting crushed while his asshole got stuffed.
"Oh, and one more thing," Linda added as she got ready to leave. "I want you to wear a polo shirt, one that comes down to about your waistline." Colin held one up. "Yeah, that'll work. Enjoy spending the next hour trying to make sure those co-ed whores don't catch a glimpse of the top of your pink panties!" Linda laughed as she left.
Colin looked down and realized that if he leaned to far in any direction, the top edge of the pink frills was just barely visible. He sighed to himself. For the first time this semester, he hoped that Erin and Heather wouldn't come to his office hours.