The Best Erotic Stories.

Tina's Hard Lesson
by Kraven

This story was split into 2 parts. Jump to any of the segments from here:
Note: This story was originally submitted as one long story
and it was only broken into 2 parts for faster page loading.

Her lacy white panties were visible through her sheer panty hose.

"Let's get you out of these," I said as I started to tug down the panty hose. She stepped back then slipped off her shoes and rolled them down herself. She stepped out of them and stood before me in just those lacy panties.

"Would you take my panties off for me?"

"With pleasure"

She put her hands on my shoulders while I slid them down. The lovely triangle of her bush came into view. It was rather thick with gold and red tints to it. I slipped the panties down her legs and she stepped out of them. I slid my hand up the inside on her thigh to her pussy. She was very wet. I slid a finger over the lips of her pussy and she lurched against me and I heard a sharp intake of breath.

"Someone else is enjoying this"

She smiled as I put my finger to my lips and tasted her.


"Now I think it's time that we finished undressing you."

I still had on my shirt and tie. It did seem being a little overdressed for the occasion. She loosened my tie and pulled it off. She tossed it aside and started on the buttons of my shirt. She leaned in and flicked my nipples with her tongue. Her tongue snaked up to my lips and thrust deep into my mouth. She held my face in her hands and kissed me deeply. I stood up so she could slide my shirt off.

"Put your heels back on. I like you in heels"

She slipped them back on.

"What you've done I believe requires some good firm punishment, don't you think?"

She looked at me quizzically.

"What did you have in mind?"

"Bend over my desk and I'll show you"

I moved the chair out of the way. She stepped to the desk and bent at the waist. The desk was lower than her hips, so it jutted her ass up in the air when her chest was flat against the desk. It was a pretty picture. Perfect for what I had in store for her. I caressed her ass and she almost purred. Then I raised my hand up and brought it down hard on her ass.



She spun around with one hand going to the red mark that was already appearing on her ass. Her ass was so white the outline of my fingers stood out in marked contrast to her milky white freckled skin.

"What the hell are you doing?"

"I am going to give you a good hard spanking, because you deserve it. Or you can get dressed and leave now. It's up to you."

I stood with my arms crossed.

She looked surprised and a little hurt.

"Do we have to do that? Can't you just fuck me? Please"

She slid her hand down lightly caressed my cock.

"Either get your ass up in the air and take your spanking, or go now"

She bit the inside of her lip. She hesitated a moment and bent back over the desk.

"Is this what you want? Is this what you deserve?"

"Yes, I've been bad and I deserve to be punished," she eked out in a small voice.

"Maybe this will teach you a lesson. Now ask for it."

"Would you spank me?"

"You don't sound very convincing. Maybe you should get dressed and leave now"

"No, please spank me, I deserve it. Please spank my ass. I need to be taught a lesson. Give me a good hard spanking, please"

"That's better"

My hand came down hard on her ass again.


She lurched forward away from my hand. Another red mark appeared. I rubbed her ass.

"We're going to make this ass nice and red. Is that what you want?"

"Yes, I deserve it"

I began to methodically swat her ass, alternating cheeks. Her cheeks began to take on a rosy glow. The swats began to get harder as we went along. I would rest a bit and rub her cheeks. They began to get nice and warm. Then I'd start in again. I could feel her tense before my hand came down. I purposely changed the rhythm so as soon as she relaxed I smacked her. She began to whimper.

"Have I been punished enough yet?"

"I'll decide that"

With that I unleashed a flurry to her now glowing red ass.





Tears were flowing now.

"Please stop, I can't take any more, please, I'll do anything you want" she blubbered now through her tears. She'd rolled onto her side.


"We're going to finish this up with this"

I opened a drawer on the side and pulled out a wooden ruler.

"No please, I can't take anymore. I've learned my lesson. No more"

"You will either take five with the ruler or we have nothing further to talk about. Is that understood?"

She slowly rolled back on to her stomach and offered her ass to me.


She howled. A red welt in the shape of the ruler appeared on her already red ass.


She sobbed.




I put the ruler away and sat back down in my chair. Tina was rubbing her ass and tears still streamed down her face.

"My ass feels like it's on fire. Did you have to use the ruler? That stings like hell"

"I decided that was necessary. Come sit on my lap"


She said as she nestled into my lap. The heat of her punished ass felt delicious on my rock hard cock.

"You enjoyed that didn't you?"

"I enjoyed it very much. Now say thank you"

"Thank you" she said and she kissed me.

"Have I earned your help yet?"

"No, now I'm going to fuck you"

"I think I'm going to like this part"

She stood up.

"Bend over the desk again"

She looked frightened.

"I'm going to fuck you now"

She eagerly took up the position that had been so painful before. She looked so inviting with her bright red ass sticking in the air. I stepped behind her and started rubbing the head up and down the length of her dripping pussy. She whined in frustration. I slid one finger into her. She was silky wet inside. I got the finger nicely lubricated and started to rub her asshole. She reached back to grab my wrist.

"No, not there please. I don't like that."

I stepped back from her. I opened the drawer and retrieved the ruler again. She saw what I had in my hand and her eyes went wide.

"No, please no more of the ruler. I can't take any more of that. Isn't my pussy and mouth enough for you? You don't want my ass, it's..... well......dirty. I'll do everything else. And please no more of the ruler."

She smiled, turned around and reached out to stroke my cock. She kissed me and ran her tongue over my lips.

"Please, let me make you feel good."

I stepped back. I looked at her shaking my head.

"Tina, this is a waste of my time. Get dressed. I'll call for the audit in the morning. You failed the test. I'll come visit you in jail."

I stepped over to my briefs lying in a heap on the floor. She looked stricken. I had put my briefs on and was reaching for my pants. She took my arm.

"No, please Brad, please don't. I'm sorry. Please don't turn me in. I'll do what you want, please."

She looked at me pleading. The tears were flowing again. I stood there with my pants in my hand.


"Bend over the desk"

She complied quickly, thrusting her glowing ass in the air.

"Slide you finger into you pussy and get it nice and wet."

She immediately slid her index finger deep into her wet cunt.

"That's it. Get it nice and wet."

She started fucking herself with her finger. She moaned.

"Now slide that finger into your ass. DO IT."

She eased the finger out of her pussy and started rubbing her asshole.


She was cringing as she slowly eased the finger in. She got it in to the first knuckle.

"Take the whole finger. I want to see your finger buried all the way in your tight little ass."

She eased it in further. Slowly it disappeared until it was fully in her ass.

"That's a good girl. I am going to give you five strokes with the ruler while you finger fuck yourself in the ass. And I want you to ask for the ruler. You deserve to be punished. You are to do what you are told immediately. If you don't, you get punished. Now ask me to punish your ass."

She had started sliding the finger in and out of her ass.

"Please," she said in a very small voice, "Punish my ass."

"You can do better than that. Convince me."

"Please, I need to be taught a lesson. Please, punish me while I fuck myself in the ass."

"Much better, you better get used to something up your ass. It won't be long until you are taking my cock up your ass. You see, this is my ass now."

With that I swung the ruler and listened to the satisfying smack it made on her hot, red ass. She closed her eyes and froze from the pain. She whimpered.

"And this is my pussy."

That was followed by another smack that raised an angry welt. She whimpered louder, as she slid her finger in and out of her asshole.

"Whose ass is this?"

"It's yours." She replied weakly.

I smacked her ass three more times in rapid succession. Her back arched, and her breath caught as the pain rocketed through her. Her finger was buried all the way in her ass when she froze. She looked absolutely delicious and I had to have her. I stepped behind her and aimed my cock at her dripping pussy. I slid the head in and rammed the whole thing home. She gasped, cried out and came, convulsing on my cock and her finger. It was all I could take. I buried my cock in her again, grabbed her by the hips and rocketed my come deep inside her, spurting as though it would never end. I felt like I had been completely drained, like along with my sperm my life force had spurted up inside of her. She had collapsed on the desk with her finger still buried in her ass. She finally slid it out and her hand fell limp beside her. I melted on top of her waiting for some semblance of energy to return.

We lay for quite some time until I finally stumbled back and slumped into my chair. Finally she pushed herself up on her hands, stood shakily and with a smile leaned over to kiss me.

"Thank you, that was amazing"

"It was wasn't it?"

"Did I earn your help?"

"Let us discuss that. There are a few other conditions. But first, let's get dressed. It makes me a little nervous to be naked here in my office"

We dressed slowly. She asked for her panties and I told her they were my souvenir. She blushed and smiled at that.

When she was finally dressed, except for the pantyhose, a little too painful for her punished ass. I motioned for her to sit on my lap.

"I can't sit right now, my ass is too sore"

"Sit now"

She eased on to my lap, grimacing as she settled her weight on her tortured ass.

"I'm going to help"

"Oh thank you"

She ignored the pain in her ass and wrapped her arms around my neck.

'Not so fast..."

I removed her arms. She looked at me quizzically.

"These are the rules and they are not negotiable. You will shave your pussy and keep it shaved. You are to wear stockings and a garter belt or garterless stockings, no panties without my express permission. Heels and skirts or dresses at all times. Your pussy, mouth and soon your ass will be available to me at any time. We will be discreet at work, but plan on spending every Thursday night with me. And any other times I choose. We will set up a schedule for repayment of the money. And the punishment you received tonight is a sample of what you will receive any time I feel you deserve it, or if it pleases me. Are those conditions acceptable?"

"Yes, and thank you, I am going to work very hard to make sure you don't regret this."

She kissed me.

"Well tomorrow is Tuesday but you can start convincing me then. I want you at my house tomorrow evening. Tonight was a little appetizer. I want a full evening. You can make me dinner."

"Yes sir"

Dinner was another story entirely.

To Be Continued...


This story was split into 2 parts. Jump to any of the segments from here:
Note: This story was originally submitted as one long story
and it was only broken into 2 parts for faster page loading.

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