From Teacher to Mistress of Dungeon

Jake was one of those guys who was really shy about everything he did. He couldn't even look anyone in the eye. So naturally he had a horrible school life, and never had a girlfriend. He moved around with the idiots. He too had lost hope of ever finding a girl, soon he moved to college. It wasn't really a good college for him with bullies all around, and hot girls who would always seem to hang around only with the best guys. He doesn't have any hopes.

He entered his classroom and occupied the front row. Though he wasn't one of those 'Hot' guys, he knew he was cute. Some girls at the back gave him a smile. Jake blushed and sat down. He didn't know how to get over his shyness. He wasn't really good at studies or anything at all. He felt like he sucked at everything. His college life was so sick. Just then Ms. Ashley walked in.

"Whoa," Jake thought.

She was the only reason he actually came to college. She was just about 26 but was so mature. She knew how to keep everyone in line, but still be really sweet. The best part about her was her body. Jake had never seen anyone like her in all his life.

He wondered why she wasn't a model. So perfect with that chocolate brown hair, those sparkling blue eyes, she always wore a coat that would project her full D breasts. She had that smooth tanned skin and those long sexy legs with black high heels. In her class Jake would be lost in a different world.

Usually everyone would think of plain sackbut Jake was a bit perverted from his child hood he had always dreamt of being controlled by a very strong confident woman, he was into femdom. He wasted his school life jacking off with the femdom porn on the internet, he wanted it in his real life as well, but he was too scared to tell anybody lest they would laugh at him.

Back in the classroom Jake was still looking at Ms. Ashley, he imagined her over him, dominating. He was suddenly interrupted from his dream when she began to hand out the papers for yesterday's test. Jake reached out for his paper stealing a glimpse of her cleavage. As usual he had failed.

"Oh, shit I failed again! What am I gonna do? What will I tell my parents? I'll be sent back to Utah" he thought.

The place was hell to him. After the bell rang Jake was surprised when Ms. Ashley told Jake to stay back. After everyone left she called Jake over to the table. Jake now got the shyness attack. He couldn't look unto her face. He stood staring at the floor.

"Umm hmm." Ms Ashley cleared her throat."

Jake I am talking to you and I expect you to look at my face when I talk to you". Jake shyly looked up, He was blushing." Damn it!" he thought. "Jake this is the fifth time you are failing on the test; you know what this means don't you? you fail for the final exam ,then you are going to go back home. You wont graduate from college...You know what that would lead to don't you?" she said. "I have no hope of you passing unless you get a special coaching. We will have to go through all the portions again. I want you to meet me after school everyday at my house before 5:00 pm. I'll take no excuses! Your failure shows my failure, so I will make sure that you pass at all costs...Whether you like it or not. Your classes start today."

With that she got up, collected her books and walked away. That left me standing there sulking. "Extra classes? OMG this is going to be one of worst parts of my life" Jake thought.

At about 4:30 Jake reached Ms. Ashley's house. It looked more like a castle in the middle of a vast garden. It had a long driveway along which Jake walked slowly dragging his bag along the floor. He rang the doorbell and waited for about a minute before Ms Ashley answered it. She was still in her teacher's clothes. Just the coat was missing; this made her look even more enchanting.

"Oh! Come in" she said. And lead him to a small room in the back of her house. It had a single bench, with a small blackboard. Jake sat down heavily.

"Good so let us begin with our first lesson's," Ashley said sitting down in front of Jake. She opened out the book and riffled through the pages. She looked up at Jake "Jake, please go get the chalk box for me. It's in the basement just below the stairs over there," she said pointing to a long dark staircase going down into darkness.

Jake stood up and slowly walked to the stairwell. He climbed down the spiraling staircase down. He looked around for the switch and flicked it on. "Oh there it is," he said to himself. He grabbed the box and was about to go back when he saw his surroundings.

He saw lot of stuff, mainly wooden frames, old furniture, and so many other things that looked vaguely familiar. He walked to take a closer look, and gasped.

"There's no mistaking," he said out loudly. The frames had straps on them, the walls on the side had whips, crops and paddles hanging, Jake immediately recognized it. She was into filmdom too. He walked to the wall and touched the whip.

"It's real!" he was looking at all the stuff when suddenly he felt someone behind him. He whirled around. "Mmm, what have we got here..." said Ashley.

"I, umm, I nothing... uuh... just... simply... uh," Jake stammered.

"It's Okay, I understand, never thought this was all real did you?" she asked. "Miss I was actually..." Jake blurted. Ashley held her finger to her lips

"Shhh, I know, you have only seen it on the internet, Wanna try? Don't worry; I will be really gentle with a beginner like you. Think about it. You want to right. I see it in your eyes." she said.

"I, actually yes, but I am scared I guess it is better just to see porn" Jake shied away." Oh come on sweetie, I told you I will be really gentle, don't you trust me?" "Uh..." Jake said.

"Come on, now be a good boy and take your clothes off and drop it at that corner".

Jake hesitantly pulled of his shirt and walked to the corner. "So what do you actually like in femdom Jake?" Ashley asked.

"Uh, actually any thing, I watch a lot of stuff. Oh, let me help you with that" said Ashley, helping him undo his jeans and tossing it to the corner. She turned him around and looked at him.

"Impressive" she said looking at his body and the 7 inch cock.

"Come here" she lead him to a table at the far end of the stone paneled basement. It looked more like a dungeon. Ashley took a leather collar which had metal studs from the table and slipped it around his neck.

"You'll really like it!" she said giving him a warm smile. She attached a leash to the collar.

"Now, I want you and the floor on all fours" she commanded. Jake slowly lowered himself to the floor. He looked so vulnerable.

"Your mistress will be back, just wait here slave boy" Ashley said as his voice trialed away. Jake was left there waiting about half an hour before Ashley returned. Jakes jaw dropped wide

"Wow", he said stunned by her beauty. She was wearing a tight fitting black corset which enhanced her D size boobs. She wore a short, tight black skirt, which looked more like a hose. Her legs looked smooth and long and had sexy looking pair of high heels. Her hair was tied in a special way; she looked like a true mistress.

"Come here slave, I don't want you to make any mistakes. You will do exactly is I command you to without any hesitation, is that clear?"

"Yes, mistress" "good, she said holding his leash as she lead him to an old sofa. Jake crawled behind her, watching those sexy legs and the beautiful high heels thudding in front of him. He waited till she was seated. Ashley pulled on his leash.

"LICK" she commanded. He moved forward with his tongue. First he gently places a few kisses on her feet and toes. Then he began taking him feet in long strokes with his tongue. He felt a sharp whack on his ass with a crop.

"I expected better than this" she scolded. Jake began licking her feet faster. He licked wildly at the toes. He could feel her toes wriggling in her high heels. He licked harder all along her feet, around the back and to her heel. He could feel her beginning to relax.

He licked, more determined to please her. After a few minutes he was presented with the other foot. After he had licked clean every inch of her feet "That's enough" she said. Jake couldn't believe all this was happening. She walked over to a clearing among all the wooden furniture. It was close to the stone wall which looked exactly like a dungeon. Long steel chains hung fro the wall. The floor had two widely spaced bolts which had leg irons attached to them.

"Ooh baby, come on stand up! You have to be better than this to please your mistress" she said.

She held him in place and ordered. "Spread those legs as wide as you can for me."

Jake spread his legs so wide that his ball sack was hanging in between his stretched legs. Ashley attached the leg irons and pulled his hands above his head and cuffed them to the chains from the ceiling.

Now she had him in an X position, and he was vulnerable from every direction. She walked to the panel on the wall and picked up a relatively thick crop and walked to him circling around him, her thundering footsteps echoing in jakes ears." Mistress, please be gentle with me" Jake pleaded.

"I'll see to it whether you are worthy of it, now open your mouth wide" she said and stuffed a big red ball gag into his mouth. She moved around him and attached the strap tightly. Jake bit into the soft rubber. Suddenly he felt something touch his balls. Ashley was now on the floor in front of him. She was beginning to take his balls in her hand and tightly tie a thin rope around it. Jake protested wildly. But the chains wouldn't give way

"What is she doing, I can't take this" he wanted to scream, the fearsome reality began to settle in. he was helpless and had to take whatever she had. He couldn't complain and had to take it whether he liked it or not. She pulled at his sack and tightly secured the rope above his balls making his sack taut and his balls compact into one tight bun. Jake screamed at the top of his lungs when Ashley gave a test smack. His scream was muffled by the gag. No one was ever going to hear him.

He heard her footsteps behind him, and then heard a loud crack of the whip. The he felt it, the pain ripped through his body from his ache almost jumped from the impact.

"I'm not impressed slave" Ashley said. She took his balls and tied the rope to a bolt on the floor,

"Try to move now, and you'll regret it". Ashley again moved behind him.

'CRACK,' he felt the next blow land on him.

He yelped as the pain from his soft ass travelled throughout his body and his balls ached as the ropes tugged.

'Crack, crack' she landed quick blows onto to his tender ass.

Jake could feel the heat, and the pain he couldn't take anymore. Ashley moved closer to Jake and gently rubbed her palm over the crimson red welt.

"Poor slave," she cooed. Then almost like lightning she landed a blow on his balls. Jake tried to scream at the top of his voice, but all that came out was a muffled cough.

The pain knew no bounds. Ashley moved back and now began to whip his bare back. She very well knew how the back was more sensitive than his ass. She landed the whip on his back and patiently waited till the red welt rose, and then whipped the welt to double up the pain.

After she was finished with his back she moved to the wall and replaced the whip. She returned with a pair of nipple clamps. She let Jakes eyes follow the clamps as she slowly dangled it in front of his eyes just to see the stark terror in them. Slowly she attached the clamps to his nipples and tightened them. She watched the nipples bulge and pulsate. Jake squirmed about in pain.

Ashley was totally enjoying his pain; she attached weights to the clamps and listened to his muffled whining. Ashley picked up a flogger and beat his bulged nipples. Jake jumped in pain and tugged at the rope attached to his balls. Ashley landed a few more strikes. Jake couldn't take it anymore. Tears welled up in his eyes. She aimed the flogger at his balls and saw his balls sway from every flogging. Finally after she was finished with him, he was hanging in his bonds, totally exhausted.

She moved behind him and untied his handcuffs; Jake fell to the ground like a sack of potatoes. She quickly pulled his wrists behind his back and tied them up. Jake was almost unconscious, his sight was blurred. Then he heard silence. He anxiously waited for a few minutes until he heard a whisper in his ear.

"You are gonna love this," Ashley gently pulled apart Jake's ass cheeks, it was tender and pink, she slowly guided her 8 inch strap-on into the hole. She could hear him groan when she pushed the dildo completely into him. She quickly drew it out and gently pushed it in while massaging his bruised ass.

Jake felt a mixture of sensations, unbearable pain and extreme pleasure. He could feel his mistress picking up pace, his insides felt so good, a relief from all the pain. He pushed back at her strap on; he was really beginning to like it. his breath grew shorter and was panting.

"Like it slave boy?" Ashley questioned. She pushed it in faster and took her hand in front of his stretched body to his cock and began to stroke it.

"Good boy, good boy I want you to come for your mistress" she vigorously stroked his cock, Jake could feel the waves of pleasure building up.

He began to moan, "Come baby come, come for your mistress. Jake erupted like a volcano spewing his come all over, Ashley continued to fuck him till he lay flat, exhausted. She removed the bonds and leg irons. Let him lay flat on the ground. After she changed, bathed and returned, Jake had managed to pull himself up.

"Oh mistress, I couldn't have had a better orgasm, Ah it was extremely painful but so gratifying". Ashley replied "You'll come back for more wont you? I want you to be my slave..."

And this vacation, back in Utah, Jake was so impatient when he looked outside his window. He badly wanted to be back there at his mistress's feet.