Cruel Tease - Chapter 4: Bring The Pain

Cruel Tease - Chapter 5: Aching For Release
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

The Cast:

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.


Colin was overcome with dread as he unlocked his office for his weekly office hours. Linda was expecting a full report after his office hours. What if Heather or Erin showed up? Colin was not looking forward to interacting with them, knowing how embarrassing it would be - even if neither of them picked up that he was acting differently.

Unfortunately for Colin, it was not long before Erin dropped by his office. She flounced in with a frustrate pout across her lips. Lips that were covered in dark red lipstick. Colin noticed, with a sinking feeling, that Erin was wearing a tight, fuzzy cardigan that was only buttoned at the bottom. It was the same dark red color as her lipstick. She had a white halter top on underneath that was straining to hold in her large breasts.

"Colin," Erin whined, "I don't understand this. I keep reading it, but it doesn't make any sense!"

Colin did his best to explain the ideas he'd gone over in the last class. It was difficult to keep his train of thought, because he kept getting glimpses of Erin's massive cleavage every time she leaned over to write a note about something he'd said.

"See? That's all there is to it," Colin managed to summarize. "Do you get it now? Do you think you'll be ready for the quiz next week?"

"I don't know..." Erin began pouting again, pushing her big red lips out and scrunching up her eyebrows, "It's just so frustrating!"

Colin wasn't sure Erin quite knew what real frustration was. His imprisoned cock was dripping pre-cum all over his swollen balls, which was lubing them up as they rubbed against the pink latex panties Linda had made him wear. Colin hadn't cum since he'd entered into this agreement - that he was beginning to regret - with Linda. Colin found himself wondering how often did a beautiful, but innocent girl like Erin got to cum.


"I'm sorry, what?" he asked when he realized he'd missed Erin's question.

"I was just saying that I'm worried about failing the quiz. I was hoping maybe there was something else you could do to help me... You know I'd be really, really grateful."

Colin squirmed uncomfortably. His blue balls were throbbing from pent-up sperm. And when he squirmed, it drove the buttplug even further up his ass, it's ridges and bumps rubbing against his distended asshole. His little cock was pinched against the tight walls of his chastity cage.


"Well, ah... what can I do to help? Do you want me to explain it again? There's some extra reading I can recommend that might explain it better..."

"Oh, I don't know!" Erin dropped her book, put her hands under her chin, and dropped her elbows onto her knees. Her large breasts jiggled, causing Colin to moan under his breath. They sat there in silence for a moment before Erin sniffled and looked up at Colin. A single tear was running down her cheek and her plump red lips were quivering.

"I just try so hard! But it's so hard to understand this! Why's it have to be so hard?" Erin asked.

Colin had reached his breaking point. He was willing to do anything to get Erin out of his hair at this point, and he was well beyond being able to do it subtlety.

"Ah, you know, Erin... I would suggest you, um, focus on the tables at the start and end of the chapter. They've got the important information for the quiz, really. Just concentrate on those and reasoning behind the formulas - you remember that section? Yeah, just... just focus on that, and I'm sure you'll be fine," Colin said, hoping Erin would get the hint that the quiz would only cover those concepts.

Erin's eyes lit up. She hopped to her feet, her breathtaking cleavage bouncing triumphantly.

"Oh, thank you, Colin! It's so nice of you to help me!"

With that, Erin planted a big, sloppy kiss on Colin's cheek. It left a giant lipstick print in dark red on his face. Colin nearly doubled over with the shooting pain from his cock and balls as blood rushed to them. Erin gathered up her books and moved to the corner of the TA office to study the tables and formulas Colin has described.

With a deep sigh, Colin turned back to his notes. He was beyond uncomfortable. He wanted to cry and cum at the same time. His moment of reflection was interrupted by a sudden movement by the door to the office. It was Heather.

Heather was on her cell and had stopped just outside the office door as she finished her conversation. Her over-sized sunglasses sat perched on her immaculately styled hair, which flowed down to her shoulders. Those shoulders were completely bare except for the thin straps of her flimsy top. Even through the doorway, Colin could tell Heather wasn't wearing a bra. Her perky tits accented the fact that her low-cut shirt read "Nasty" right across her chest. Heather also had on exceedingly tight low-rise jeans and her belly button ring had a light chain that ran around her waist.

Heather finished up her conversation and walked into the TA office. Erin didn't look up, but it was everything Colin could do not to beg her to leave! Then Colin noticed that Heather didn't look very happy.

"Everything alright?" Colin asked.

"Yeah, I guess. I mean, I had a fight with my boyfriend and my best friend today," Heather said with an annoyed look. "I don't know. Tyrone, my boyfriend, has just been so possessive lately. He just doesn't understand that I'm going to talk to other guys - there's just nothing he can do about that. Like, what am I supposed to do, not talk to Jamal or Tyree when I see them at the the gym? Or not let some hot guy buy me a drink at the club? He's just so jealous. And I'm totally loyal to him, most of the time! It's not fair!"

"Yes, I could see how..." Colin started to say before Heather jumped back in.

"And then my stupid friend, Nikki. She saw me go upstairs into one of the bedrooms at the sorority with her boyfriend and now she's all, 'You need to stop sleeping with my boyfriend!' I mean, whatever. I only slept with him because he's on the basketball team. It's not like he's one of me regular boyfriends, right? So my stupid sex life is totally messed up, and I'm all horny and stuff, but it's all dumb, so whatever."


"Hmmm," said Colin uncomfortably. He decided to try and route the conversation back to safer topics. "So were you thinking that studying would take your mind off of all of this... drama?"

"Not really. I wanted to drop in and tell you that I just haven't been able to study with all of this craziness around my life in the bedroom. So I don't think I'm going to pass the quiz next week without some help... Do you think you could help me?" Heather asked, arching an eyebrow. "With... either of my problems?" She added with a sly grin.


"Well, I could help you go through..." Colin started to say.

"No, isn't there some easier way than studying? Something that would solve both my problems at once?" Heather asked. She was hinting, of course, that Colin offer the quiz answers to Heather in exchange for sex. Heather secretly hoped Colin would find a way to ask her to make a deal, because she found him oddly attractive... in a nerdy sort of way.

"Um. Well. I'm sure..." Colin trailed off. He knew that Heather was providing him with an opportunity to act one of his favorite jerk-off fantasies - at least it had been before Linda locked him in chastity. But that was the problem itself. Even if Colin accepted, he wouldn't actually be able to have sex with her, because there was no way Linda would allow it.

"What's the matter, teach?" Heather said with a grin. "Not interested in girls?" Colin started to blush. "You know... you never hit on me in class. All of the other guys hit on me - but not you. Maybe you're more into penis? Hmmm?" Heather teased.


"Who's into penis?" Erin asked, confused as she looked up from her book.

"I think Colin might be. He never hits on my in class," Heather explained.

"Oh. I thought all the guys hit on you. Don't you think Heather's hot?" Erin asked Colin. "And don't you think I'm cute? You never hit on me either. Don't you like us? Do you think we're... ugly?"

"No, no, no. Not at all. I... um," Colin was realizing that he was painted into a corner. "Obviously, I think you're both very attractive young women. I just... it would be unprofessional."

"Oh, so you do think we're hot?" Heather said as Erin looked on from her chair.

Colin, now desperate to change the subject, suggested that Heather study the same sections that he had mentioned to Erin. Before Heather had a chance to harass him further, he realized that his office hours were almost over.

Colin wrapped up their conversation as he shuffled papers and gathered his books. He was glad to be heading back to home, where he would hopefully be unlocked by Linda and allowed to cum. While he was thinking about all of this, Colin stood up and noticed a sheet of notes he had dropped. Colin turned from the two girls, who were also gathering their papers, and bent to pick up the notes.


As he started to stand back up, a wave a fear washed over Colin. He realized in one terrifying moment that his shirt had pulled up his back just a little as he had bent over. Erin and Heather had just gotten a clear look at the pink latex panties Linda had made him wear...

Colin stood up quickly and slowly turned around to face Erin and Heather. He hoped desperately that the two women he had fantasied about all semester had somehow missed seeing the obvious evidence of his sissihood. Unfortunately, when he turned he saw Erin with a poorly concealed look of amusement on her face. When he made eye contact with her she quickly looked away, embarrassed.

Then, with mounting dread, he looked at Heather. She was standing with one hand on her hip and the other over her mouth. She was making no effort to hide her laughter. Colin put his head down and fled out the door.