Story: Cruel Tease - Chapter 6: Making It Worse

Cruel Tease - Chapter 6: Making It Worse
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 let Linda lock him in chastity
Lindsay - Colin's girlfriend, 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 6: Making It Worse

Colin called Lindsay as soon as he got back from his class. He told her what was going on. His balls were aching. He could feel the throbbing so much, it was hard to focus. It didn't help that what Heather had said to him absolutely terrified him. "Who better to tease than a man that we know can't do anything about it?" It was true, of course, but hearing the hot, snarky blonde say it to his face... well, there was something in how open and direct Heather had been that had petrified him.

"It sounds like you've been through a lot," Lindsay admitted. "And how long have I had you locked up? A couple of weeks?"

"It's been three weeks," Colin said with a cringe.

"Hmm. It doesn't seem like that long to me... but I bet it does for you!" Lindsey laughed. "Well, it's Friday, so maybe I should come over. I could spend tonight and Saturday night, then leave on Sunday. How does that sound?"

"That would be great!" Colin said.

He was starting to feel better about things. He shouldn't have.

Lindsay arrived a few hours later. She handed Colin the duffel bag she was carrying as he let her in. It was getting warmer out as spring approached, and Colin noticed that Lindsay was taking full advantage of the weather. She was wearing a pair of incredibly tiny shorts and a flimsy halter top. Her red hair was pulled back in two braids, so keep it off her shoulders and help her stay cool.

"You can put that bag anywhere," Lindsay said as she looked around Colin's room. "It's beastly hot out. I'm all gross and sweaty, just from walking here from my car. Ugh. I know, why don't you help me with that while I relax for a bit?"

"Sure. How can I help?"

"I brought a book to read. Why don't you turn on the ceiling fan, and I'll stretch out on the floor and read for a bit."

"Ok. That sounds like a relaxing way to start the weekend. I just started this great book-"

"Oh, you won't be reading," Lindsay added. "Put some blankets on the floor, so I can read comfortably. Then hand me the bondage tape from my bag. I got pink, because I wanted it to match your cage!"

Colin handed her the tape, and spread out a few blankets. He added a few pillows for Lindsay to rest against.

"That looks great. Now turn around so I can tape you up," Lindsay said with a smile.

Colin turned and Lindsay positioned his hands so that each grabbed the opposite arm just above the elbow. Then she wrapped his two arms together with the pink tape. When she was done, Colin couldn't move his arms at all and his hands were completely covered in tape.

"There we go. Just how I like you - restrained!" Lindsay said with a giggle.

Then she hooked her thumbs in her shorts and slid them down. She wasn't wearing any panties. Colin whimpered as his cock struggled to get hard in it's pink prison. Lindsay turned her back to Colin and rubbed her ass on the crotch of his pants. Colin couldn't feel anything - it was maddening!

"I got so sweaty out in that heat," Lindsay said as she kept grinding her ass into Colin's caged cock. "While I'm reading on my stomach, I want you to clean all of the sweat off of my ass. Bury your face in my ass crack, and lick me clean until I tell you to stop. And I want you to really get in there - I'm very sweaty."

Without another word, Lindsay turned around and lay down on the floor. Her tight, bubblebutt stuck up. Her perky cheeks were covered in a light sheen of sweat that made them  look even more inviting. Ignoring the awkwardness of this arms, Colin got down on his knees behind Lindsay . Not wanting to disturb her, he flopped down on his stomach so that his head was between Lindsay's knees. Then he slowly inched forward until his face was right at her ass crack. Lindsey ignored him completely.

Her ass cheeks were glistening with sweat. They moved ever so slightly with every breath she took. They looked soft, but muscular at the same time. He could just barely make out her tight asshole between her cheeks. The smell of perfume and light sweat filled his nose. He lay with his face right at her ass, transfixed by the view.

"Quit stalling and get to work, asslicker!" Lindsay commanded without looking up from her book.

Lindsay knew what a crippling ass fetish Colin had. She also knew that, since she'd kept him locked up for weeks and weeks, his balls must be incredibly full of built-up cum. And she was planning on turning Colin's backed-up balls against him. Teasing him into a frenzy, only to deny him more. Her plan was to repeat the process over and over, until he had the worst case of blueballs any man had ever had to endure.

"Kiss away the sweat. Then lick me clean. Pay special attention to me ass crack and asshole. Try to really get in there and get it clean," Lindsey said with a giant grin.

Lindsay didn't have to look up from her book to know what her orders were doing to Colin. His mind was numb, he was so confused. He didn't know if he should be ecstatic at the prospect of getting to be so close to her ass, humiliated for being so excited by that idea, or frustrated by his inability to get hard while he was so excited.

Finally, his desire to obey his keyholder won out, and Colin began softly kissing her round ass cheeks. He tried to be systematic about it, wanting to do a good job, so he worked from left to right, then up slightly, then right to left, then up slightly... Despite the desperate throbbing from his locked up cock, Colin was in no hurry. Even in chastity, he couldn't think of a better place for his face to be than planting kiss after kiss on Lindsay's tight ass.

It took Colin a full half hour to cover both of Lindsay's ass cheeks with soft kisses. She had ignored him the whole time. It was as if he wasn't even there. Despite his willingness to debase himself for her amusement, her book still rated more attention than he did. Even though Lindsay was completely ignoring him, engrossed in her book, the act of serving her in such an intimate, yet dirty, manner was beginning to take its toll on Colin. Being so close to her sweet ass that it was the only thing he could see didn't help either. If Colin had been able to see behind himself, he would've noticed a sizable pool of pre-cum forming where the tip of his cage rested on the floor.

With a deep breath to brace himself, Colin started in on the main course - Lindsay's ass crack and asshole. Knowing that his chance to finally cum was completely in Lindsay's hands, Colin was prepared to do his absolute best to please her. Lindsay had told him several times that what she enjoyed most about Colin eating her ass, aside from the physical pleasure, was how humiliating the act was for Colin. With that in mind, Colin decided to be even more thorough on Lindsay's ass crack and asshole, knowing that she would appreciate that he was intentionally making his humiliation last longer. The more thorough he was, the more degrading he was making it for himself, which in turn made it more amusing for Lindsay. He started at the top of her crack, and moving slowly, deliberately made sure he licked every square centimeter of her ass crack - twice - as he moved down.

Lindsay continued to read, ignoring him completely.

After awhile, Colin finally reached the top of Lindsay's asshole. He decided it was a good idea to leave the "best" for last, and moved down to Lindsay's taint. Even though there was much less space here to clean, Colin had to be very careful. He wanted to clean as much of Lindsey succulent ass as possible, but he also knew that if he even brushed against her pussy, she would punish him severely.

Slowly and carefully, Colin licked Lindsay's taint until it glistened with his saliva. He tried to ignore the way Lindsay's pussy was dripping from all of the attention to her ass. She would never let Colin know it, but Lindsay was unbelievably turned on by Colin's wet tongue and his eagerness to debase himself. Lindsay focused on pretending to read her books while Colin continued to lick and kiss with his warm tongue.

Finally, Colin was ready to start licking Lindsay's asshole. Trying to be as gentle and loving has he could, Colin began to massage the rim of her asshole with his tongue. He kept his tongue very wet, so that soon the entire area around her hole was dripping with saliva. Each and every bit of Lindsay's asshole was explored by Colin's tongue. He diligently worked his tongue into every fold and crease, deliberately trying to illustrate how committed he was to serving Lindsay's demanding ass.

For nearly half an hour, Colin serviced Lindsay's asshole. He circled her tight pucker with his tongue, flicked his tongue around the sensitive edges of her asshole, and massaged her hole with the tip of his tongue. Finally, Lindsay interrupted Colin's excruciatingly thorough licking.

"Ok. That's good enough for now," Lindsay said with a chuckle. "Why don't you just rest your face on my ass while I finish reading? Grab a quick nap - I'll probably finish my book in an hour or so"

Colin's tongue ached so badly, he was just happy to rest. He turned his head sideways and put his cheek on her right buttcheek. Colin discovered quickly that resting that way was nearly impossible. The angle his neck was at, rising from his body on the floor to Lindsay's perky asscheeks was just too sharp when his head was turned to the side. After fidgeting a little, struggling to get comfortable, a slow realization dawned on Colin. This wasn't an accident. Lindsay knew there was no way for Colin to turn his head sideways and use her asscheeks as a pillow. There was only one way for Colin to comfortably rest behind Lindsay.

Colin sighed as he resigned himself to the inevitable. He realized that the only way to be comfortable while Lindsay read was to lie face down, with his face firmly buried in her buttcrack. Worse, he knew that Lindsay had planned all of this. She was making him lie still with his nose on her puckered asshole and his face jammed between her cheeks on purpose. She knew it was the only way for him to avoid sharp pain firing down his neck from the awkward angle. As he gently worked his face into the position Lindsay clearly wanted, Colin began to wonder if Lindsay was even really reading at all. After a few minutes of lying like this, Colin slowly drifted into a light sleep. His dreams were filled with images of Lindsay kissing and licking his pink cage, a cage that kept getting smaller and smaller around his swollen blue balls and trapped cock.

After what must have been a few hours, Colin woke up from his nap to the sound of a camera phone. The first thing he noticed wasn't the sound though, it was that his face was resting on the hard floor instead of Lindsay's soft ass cheeks. As that registered with Colin's groggy mind, he also noticed the camera sound that had woken him up. Yawning, he raised his head up off the ground and looked around for Lindsay. What he saw made him freeze in terror.

Just as he had feared, Lindsay was standing behind him with her cell phone, taking pictures of him on the floor. And what a sight he was! His arms were still tightly bound in pink bondage tape. His over-the-top sissy panties were wedged up his ass. And his cage...

His pink chastity cage had been painfully squished back between his legs so that he could stretch out on the floor without having it underneath him. While he slept, Lindsay had pulled his frilly pink sissy panties to the side so his cage was clearly visible. And now, after prolonged chastity and spending so much time excited by servicing Lindsay's ass, there was an enormous puddle of sticky precum that had dribbled out of his little locked cock.

"Morning, sleepy head!" Lindsay said with a laugh. "I got bored while you slept, so I decided to take some pictures of you for fun. I pulled your panties out of the way, so I could get your lil' cage in the picture too... Looks like somebody made a little loser precum puddle! Ha ha ha."

Colin's heart sank as Lindsay started typing on her phone as she picked up a sheet of paper off of Colin's desk. He knew what the paper was without even seeing it. It was the list of student contact info for the course he taught. The course Erin and Heather were taking. Colin could hardly breath.

"Oh, look! There's only one Erin and only one Heather in your sections. I guess that must be the two girls who've threatened to, um, take advantage of your little situation, huh?" Lindsay said with a giant smile. "I figured you had to have the a way of contacting your students around here somewhere. Since Heather and Erin have been nice enough to help me make your life even more miserable, I think would be fun to send them a quick thank you note. So I wrote it on your ass. That's why I gave you a pantie wedgie - I needed you little butt exposed so I could write on it with my lipstick. Here, just let me attach the picture... there we go! All sent! Now, what else should we do today?"

If Colin could've seen the picture Lindsay had just sent to Heather and Erin, he would've seen that the message Lindsay had written to them on his butt read, "Please tease and abuse him! - Lindsay =)"