Story: Cruel Tease - Chapter 5: Aching For Release

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 DecisionThe Cast:
Colin - a grad student who was silly enough to let Linda lock him in chastity
Linda - a redheaded cocktease with a vicious dominant streak
Erin - a sweet, innocent brunette college student. Colin is her TA.
Heather - a bratty, bitchy blond college student. Colin is also her TA.
Chapter 5: Aching For Release

"So how was it? Get asked any hard questions by cute sorority sisters?" Linda asked when Colin got back to his place.

Colin shook his head "no" while staring at the floor. He couldn't bring himself to tell Linda how embarrassed he was. In his hurry to get away from Erin and Heather, he'd accidentally flashed the pink frilly panties that Linda had made him wear. Even though it had just been for a second, Colin was sure that they had both noticed.

"Don't lie to me, little man," Linda said with a smile. "I can tell something is up. Strip down to your new panties while I put on my new strap-on. Let's replace that buttplug with my new rubber cock... I'll see if I can't fuck the truth out of you!"

Linda did just that. Once he was naked, she handcuffed him. Then she bent him over his bed and pulled his tight pink panties down. She berated him for not being a "real man" while she spanked him and smacked his ass cheeks with her strap-on. Once she had reddened Colin's cheeks a bit, Linda put the head of her strap-on cock right on his clenched asshole. She started making little thrusting motions, so that Colin could feel her cock poking at his ass. In between pokes, Linda would spit on Colin's asshole.

"The only lube you get is my spit, because that's all you're worth. When I see you, I just want to spit on you. You're so lucky that I'm going to give you any lube at all, faggot. I'm actually kinda surprised that my cock didn't just slide right in - I figured you'd be pretty loose, since I'm sure you get assfucked by dudes all the time when I'm not around!"

With that, Linda shoved her strap-on into Colin's poor hole. His asshole stretched frantically to accommodate the large rubber cock. Linda started to fuck him with a steady rhythm. Her hips bumped up against his as she drove her cock balls-deep into his ass. Then she would grind against him with the strap-on still buried, before pulling completely out and starting over.

After about ten minutes of this, Linda decided that the whole ordeal wasn't painful enough for Colin. She was afraid that he was becoming desensitized to her giant strap-on's invasion of his tight pucker. So she quickly thought of a way to up the ante - she reached underneath Colin when she had her cock all the way up his ass and grabbed his balls!

They were so full of backed-up cum, it was easy to do. They were so swollen and the pink chastity belt held them tightly, but Linda managed to get one hand around them both.

With a cruel laugh, Linda began slamming her strap-on in and out of Colin's battered asshole. Over and over, she pulled completely out, then yanked on Colin's balls to add leverage to her next thrust. Colin was in tears after just a few seconds of this treatment. His sobbing drove Linda to fuck his ass even harder. And she began to squeeze Colin's swollen blueballs as well as pull on them. Linda was enjoying herself immensely.

"Tell. Me. What. Happened!" Linda said, punctuating each word with a deep thrust and a hard squeeze.

"I'm so sorry, "Colin started to blubber. "I tried so hard! B-b-but two of my students w-w-were there and they were asking me q-q-questions... And, and I th-th-think they saw my p-p-panties!"

Colin was crying now. He didn't even notice the fat rubber shaft up his ass or the constant pressure on his balls anymore. Re-living his humiliating experience was just so demoralizing! Linda realized this was the perfect time to find out every embarrassing detail of Colin's humiliating experience, while still pounding his ass and crushing balls.

"Ha! [thrust] I knew something happened! [thrust] Which of your students saw your frilly [thrust] pink [thrust] panties [thrust], cocksucker? [thrust] " Linda asked Colin.

"Erin and Heather, " Colin answered as he tried to hide his face in his bed.

"Are they hot? [thrust] [thrust] [thrust] I bet they are..."

"Y-y-yes, they're hot," Colin admitted. "I tried so hard to get rid of them, so they wouldn't figure it out... but... they did anyway," Colin said as he buried his face in the mattress.

"What did you do to try and get rid of them? Were you impolite to your student hotties?" Linda asked in a threatening tone. Before Colin could answer, she pulled back and drove her right fist squarely into his trapped balls.

"Ohhh," Colin moan. "No, miss! I told them what to study for the exam. I didn't give them the answers, just suggestions. I was hoping they'd leave once they knew what to study."

Linda shoved her strap-on up Colin's asshole to the hilt as she laughed, "And what did Heather and Erin do when you told them what to study?"

Colin sobbed, "They wouldn't leave! They started teasing me about how I never hit on either of them, even though all the other guy students and TAs do... They kept asking me if I even liked girls..."

Linda laughed at that comment, since she was pounding away at Colin's ass with her strap-on as he mumbled the story. She made sure to really throw her hips into the next couple of thrusts. Linda thought it was important to make Colin especially uncomfortable as he shared his embarrassing story.

"Well, that gives me a great idea, subbie," Linda said with a giggle. "You're going to ask those two young, hot girls to stop by right after your next session of office hours ends. When they show up, I want you to explain that your mistress wouldn't approve of you hitting on them. Tell them about how I have your locked in chastity and how you're entirely subservient to me. Don't get into details or gross them out. Just explain that you're not allowed to respond to their advances. Then we'll see what happens... Now I'm going to lie down and you're going to straddle my strap-on. Are you ready to bounce on my cock?!?"

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Colin did as Linda instructed. Later that week, he pulled Erin and Heather aside after class and asked them to come by after his next office hours. That was how he found himself nervously standing in an empty office with the two beautiful college girls.

Before he'd left for the meeting, Linda had given him a long handjob with lots of lube. With Colin tied to his bed, Linda's fingers were tortuously slow. The speed and lack of friction kept Colin from getting close to cumming. Then, when she was satisfied by the amount of pre-cum his cock was drooling, she shoved Colin's cock into his pink chastity cage. She crammed the fat, pink buttplug up his ass, and made him pull the same pair of frilly pink panties over it all. Only then was he allowed to go meet Erin and Heather.

Amazingly, Erin and Heather reacted better to Colin's admission and apology than he could've hoped. Rather than running straight to the dean, both of the co-eds met his dark secrets with laughs and cruel smiles. Erin had blushed and looked at the floor a lot to start, but had warmed to the conversation as it went on. Heather, on the other hand, had stared unblinking with a malicious happiness that had frightened Colin. What ideas were in that beautiful young woman's head?

Colin thanked them for their time and for being so understanding. Erin just smiled like a ditz with too much on her mind. Heather had just laughed and walked out.

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Linda was very happy to hear the news of Erin and Heather's reaction. She demanded updates of any "out of the ordinary" interactions between Colin and the students. Colin had secretly hoped that Erin and Heather would switch to other lab sections, but there was little hope of that now!

At the next class after their private meeting with Colin, Erin and Heather began taking advantage of the situation. Both of them stopped handing in homework. Colin had secretly hoped they would both stop coming to class, trusting that he would pass them out of fear of being blackmailed. But they kept coming to class…

Erin, demure as she normally was, began wearing low-cut tops that showed off her large tits. The male students got an eyeful, but none of them were quite as frustrated as Colin was by Erin's new found willingness to flaunt her cleavage.

Then Heather came up to Colin after her section was done for the day. She licked her lips, which Colin had noted at the beginning of class were covered with a thick coat of shiny pink lip gloss. They looked so wet and full, it made his locked up cock throb. Just the thought of her using that tongue on a cock – any cock – made him sweat and stammer.

"Well, Colin, how are things?" Heather asked as she looked around the emptying classroom.

"Th-th-things are good," Colin said nervously. 

"Sure they are. Listen, cutie, I've got some bad news," Heather said with a giggle and an evil smile as she motioned to the now-empty classroom. "Unfortunately for you, Erin and I have decided that your lab sections are an excellent place to tease our new pet TA. I mean, who better to tease than a man we know can't do anything about it? And what better time to harass our chaste toy than right in the middle of his class?"

Colin paled at the thought of being teased by both of his students, in addition to suffering all of the punishment and teasing that Linda would continue to give him. 

Heather leaned into Colin and put her wet lips next to his right ear, causing his blood to boil. Then she put her right hand lightly on his cage, rubbing it ever so gently through his pants. Colin wanted so desperately to get hard, he almost started crying.

"Here's the funniest part," Heather said breathlessly. "We don't have your key. So no matter what we make you do or how much you beg us… we couldn't let you cum if we wanted to!"