Modern Day Sentimental Education


He walked to the bedroom. For a moment, he wasn't sure if this was the right room, for on the bed were clothes he thought for someone else. Diane had laid out what looked like a black leather corset. Straps hung from the sides. He had seen stuff like this in lingerie catalogs. Next to it was a pair of black silk stockings. On the floor, he was amazed to see a pair of black leather thigh high boots. Oh my god. Did she really want me to wear this?

His hands shook as he slipped into the corset. He pulled on it very hard. It slid up his smooth stomach. It was so tight his breath did not come easily at first. He was thin, but the corset made his sides come in even more. Next, he sat on the bed and, as he had seen his mother and girls in movies do, he rolled up the stockings and unrolled them over his legs. He had nice legs, or so he had been told, from running. They silky material felt wonderful, he had to admit, over his smooth skin. With difficulty, he fixed the straps to the tops of the stockings. Everything seemed so taught. His cock rubbed against the leather of the corset. He eyed the boots. Could he even walk in them? He slid his foot in the first boot and, amazingly, it fit. Had Diane been planning this? The long zipper sealed the leather on his calf and thigh. It was tight. He touched the boot. It was of very soft leather. He loved the feel and smell of them. He extended his leg, admiring the boot. He put on the other one. Now, with trepidation, he went to his feet. His first few steps led to him falling against the bed. He tried again. The boots had what seemed just over 5" heels. They forced his hips forward and made the stockings and corset even more taut on his body. He tried to mimic the way girls walk in heels. That seemed to help. He swung his hips. For some reason, it was fairly easy to him. This troubled him. He looked in the bedroom mirror. He wanted to cum. He looked so, well, sexy. Pretty, even. He had a nice body. Sexy, for a guy; yet, the outfit added this wild, androgynous element. He slowly stroked his cock as he looked from the boots to the corset top. He turned to look at how the garter straps of the corset framed his ass. He wanted to cum, but knowing Diane would be displeased, he stopped.

He walked down the hall to see his Mistress.

The sound of Chris' heels echoed on the hardwood floors. When he entered the living room he was not prepared for the site before him. Diane had changed, as well. Like Chris, she was wearing a pair of black leather thigh high boots, but her heels seemed even taller. A tight leather corset and garters attached to shiny stockings peeked above the tops of the boots. On her arms she wore shoulder length black leather gloves. They were so smooth and tight looking. Her makeup was even more severe. But, it was what she held that made Chris' heart skip a beat. She was tapping a black leather riding crop gently against the side of one of her boots as she fixed her eyes on him. His Mistress approached him.

"My, my, how sexy we look."

Diane reached out to run her crop lightly around his cock and balls.

"Mmm, and still so very hard. One would get the notion you are quite pleased with your outfit. Is that so little boy?"

Chris looked down at the ground, averting his eyes from his Mistress.

"Look at me!"

Diane reached up to grab his balls with her gloved fingers and squeezed them.


"Look at me!"

Chris raised his eyes. Diane slowly let go of his testicles.

"Now, tell your Mistress how much you like your outfit."

"I...I like my outfit Mistress."

Diane flicked the crop against his erection. Chris flinched.

"You can do better than that."

"I love my outfit Mistress!"

Diane walked around him, tracing the crop on his skin.

"Yes, that's much better. It's obvious you love your outfit. But, it's not quite complete yet, no?"

She walked to her bag and pulled out a tube. Chris followed her stiletto boots with his eyes. She walked back towards him.

" Now, bend forward."

Diane reached out and slowly ran the tube around his lips.

"Good, now rub your lips together."

Chris did as she said, feeling the creamy lipstick spread on his lips."

"Oh, yes. My, you are a very pretty boy Christopher. Such sexy lips."

Chris shivered.

"Thank you Mistress."

Diane smirked. She walked back to her bag and took out her cigarettes. Extracting one, she lit it in her red lips and then walked to Christopher.

"Open your mouth!"

Chris saw Diane's black leather gloved hand place the long, white cigarette in his lips."

"Inhale, now!"

Chris drew on the cigarette and coughed.

"Slower slave!"

Chris tried again, drawing just a little bit, exhaling a small stream of white smoke. He held the burning cigarette in his hands, noticing the red lipstick marks on the filter."

"That's much better. Since you seemed so enamored of my smoking I'd thought I'd let you have a try. Now, hold it as I say."

Diane instructed him how to hold the cigarette up by his side, elbow bent, like a girl.

"That's better. Look at you. You ARE a slut, Christopher. Don't you think so?'

Chris just held the cigarette, without answering.

"Speak up!"


"Yes what?'

"Yes, I am a slut, Mistress."

"Yes, you are. Now, show me your slut walk as you smoke your girly, long cigarette. Only sissies smoke such cigarettes."

Chris blushed deeply. He walked, trying to exaggerate his hip swing as he smoked the cigarette and held it like a girl.

"That's it. See, now put your weight on your toes. You are quite good at this. Such an easy slut to train. Maybe I should call your mother and let her know."

Chris froze in his tracks.

"Oh god, no!"


"Please, no Mistress."

"How dare you tell me what to do?"

"Please, I'll do anything Mistress, just don't tell her."

Diane paused for a moment. She was dripping with excitement as she watched her young slave.

"Hmm, anything? You may regret you said that. We'll see. Take another drag on your cigarette and hand it to me."

Chris drew on the cigarette again and blew the smoke out of his pursed lips like he saw girls do. He handed it to Diane. She held it then took a long drag, blowing the smoke at his face. She walked to the coffee table and stubbed it out.

"Come here. On the floor. I want you on all fours."

Slowly, Chris walked over to Diane and got to knees. His high heels made it very difficult to hold his position. Diane sat on her couch and then put her booted legs up on his back.

"Hold that position slave. Don't you fucking move!"

Chris looked at the floor as he felt the weight of his Mistress's legs on his back.

Diane picked up the phone and dialed a number.

"Hello Maureen?"

Chris started to shake.

"It's Diane, how are you? Very well. Listen, I wanted to let you know I'm free for lunch next Thursday and I'd love to join you. Great, then 1:30 at Chez Henri's. See you then."

Chris sighed.

"There, there little one."

Diane tapped his head with her crop.

"I wasn't going to tell her now. But, if you fail to please me, I might have to take some photographs to share with her. Surely she would want to know what a sissy slut slave her son is."

Chris shook.

"Please, oh god. Please Mistress. Please don't do that."

"We'll see. Now, get up!"

Chris struggled to his feet, wobbly on his stiletto heels. Diane walked around him. Her leathered gloved fingers stroked his cock gently as she glared at him. He felt his cock grow painfully hard. She traced the head and slit of his cock.

"Hmm, what's this?"

Diane held up her finger, revealing a shiny sticky fluid on her black leather gloved fingers.

"Pre cum? You better not explode slave. Lick this now!"

Diane shoved her leathered fingers into his mouth. Chris sucked his fluid off the gloves. She laughed.

"Hmm, I knew you would like it you little slut."

Chris lowered his head.

"Now, Christopher, after talking with your parents and observing you, I've come to the conclusion that you are a bit too full of attitude for your own good. We all noticed, at the party, the smug way you stood off to the side and looked at us. One semester of college does not a smart-ass make. You little twit. Someone needs to beat yourself out of you. Don't you agree?"

Chris mumbled.

"What's that?"

"Umm, I don't know Mistress."

Diane reached up and twisted his nipple very hard.


"Now, answer me properly you fucking slut!"

"I need it Mistress."

Diane released his nipple.

"Oh, yes you do. More than you even know. Kneel on the couch. Get your fucking ass in the air!"

Chris slowly walked to the couch and reached out to the backrest to steady himself. He placed both of his leather clad knees on the cushions.

"Now slave, it's time for your lesson. After each beating I want you to count. Do you understand?"

"Yes Mistress."

His heart beat faster. His mouth grew dryer.

"Good, now stick that slut ass out for me."

Chris lowered his head to the cushions as he shifted his rear out. He never felt so exposed and helpless in his life. The cool air of the house meeting his naked rear.

He wasn't sure if he could hear the sound of the crop coming through the air. The resulting pain cleared any other thoughts.



Diane paused, feeling her loins flood with her juices. Her nipples rock hard above her corset.

Slap! "Unh, two!"



"Oh, very good my slave." Slap!

Chris paused.

"Ugh, Four!"

And on she went. The blood under his skin so apparent. Diane knew he wouldn't sit without pain for some time. Around the tenth stroke she heard his muffled cries.

Chris clenched his teeth. He could feel the tears streak down his cheeks. Partly the pain and partly the realization of how hard he remained. This warmth that spread in his balls and shaft. He rubbed his cock on the cushions of the seat. His mind lost in a haze of pleasure and pain.

Slap! "Ahhh, eleven! Oh god, more....Mistress Diane...please."

He was crying outright. She stopped. Diane leaned on the couch and caressed his hair.

"Shh," she said as she stroked him gently. "There, there my sweet Christopher. It's okay."

His sobs continued, but slowly subsided as she kissed his tears. She pulled his lips to hers and they kissed. Here tongue snaked in his mouth, marveling at the feeling of his lipsticked lips on hers. He moaned softly. For quite some time they let their tongues caress one another's as their passion grew.

"Oh Mistress. I, I feel so different."

Diane kissed his watery eyes.

"Yes, I'm sure you do. I want you to belong to me Christopher. As my slave."

"Yes. I want that, too. I'm scared Mistress, but, I..."


"I love you Mistress."

Diane kissed him deeply again.

"In time you will love me, but now I think you are just overcome in the moment. Your training is far from complete, our bond not yet established."


Diane laid her leather gloved finger on his lips.

"Shh. No more talking. Now, get up Christopher."

Chris stood to his wobbly feet, feeling a tremendous head rush.

"Now on your knees before me."

Chris kneeled before his Mistress. Diane reached out with her gloved hand and pulled the back of his head into her leather covered sex. At once, Chris felt her wetness around and against the black leather thong she wore. He inhaled the strong scent of leather and her cunt. He moaned against her sex.

"Lick me slave!'

Diane pulled on the back of his head and ground her sex on his mouth. He felt his nose gnash into her pubic bone as he not so much gave her head as she fucked his face.

"Ohh...ohh......very good slave...oh...Chrisopher....."

He could feel her body shake. She must be close, he thought.

'Ahhhhh..yes, that's it, yes! Yes..Unnn..fucking yes!"

Diane shook against his mouth. He felt her girl cum as it dripped down her legs..

"Lick me there Christopher...all of it. Clean me my sissy boy."

Chris gently lapped at Diane's cunt. He was inexperienced at pleasing a woman there, but soon learned he enjoyed the taste of his Mistress's juices. His lips were nearly numb from the pressure her mound placed on them.

"Mmmm..yes, very good."

Diane pushed him back hard.

"Enough. Now, fetch me my cigarettes!"

Diane leaned back on her couch. Chris pulled out one of her cigarettes.

"Light it for me!"

Chris placed the very long cigarette in his red lips and lit it slowly.

"Look at you with that girly cigarette. You like to suck on it, don't you?"

Chris looked down at the ground.

"Yes, Mistress."

Diane laughed.

"Soon we will find out what else you like to suck on."

Chris swallowed hard.

Diane reached out to take the burning cigarette from him. She took a long, luxuriant drag and exhaled a full cloud of white smoke from her crimson lips. She felt delicious. Her eyes fell to Chris' still very erect cock.

"Hmmm, would my slave like to cum?

"Please, yes Mistress."

"Very well. Move closer and rub your cock against my boot."

Chris put his legs to either side of Diane's right leg. He moved against her so that his smooth, hard cock was rubbing on the black leather of her boot shaft."

Diane felt herself grow wet at the feeling of his cock through her boots. A maniacal, lustful grin spread across her face.


Chris was moaning softly as he moved his hips more quickly to rub his cock harder on his Mistress' boots. He was so close. Diane exhaled a cloud of smoke in his face. He felt her leg shift and move back and forth, urging him along and making more contact with his cock. The leather hot with friction and slick with his juices as it caressed him. He felt an explosive warmth move within him.

"Oh god!! Mistress I'm going to cum!!!"

Diane felt the warm spurts of his fluid through her boots. She sucked hard on her cigarette, moaning softly on her exhale. Ribbons of cum exploded from her slave, coating her boot shaft.


Chris continued to move his cock back and forth against the cum streaked boots. Diane flexed her toes in the boots.

"There my slut slave. Come here."

Chris leaned forward and their lips met. Diane shoved her tongue deep in his mouth. Chris sucked hard on it as he pressed his cock into her boots. She pushed him back. She pointed to her boot.

"You have made quite a mess slave. Now, clean it up. These are very expensive boots and I don't want to see one trace of your sissy cum on them. Do you understand?"

Chris hesitated. Diane pressed the stiletto heel of her other boot into his cock.


Chris immediately lowered his head and lapped at his cum. At first, he resisted the slightly bitter stickiness but soon he was licking and swallowing. His tongue sought all remnants of his orgasm. He looked at Diane's boot shafts glistening with his saliva.

"My, my you are quite the cum eater."

"Yes, Mistress."

Diane laughed. She patted the seat cushion next to her.

"Come, come."

Chris got up and sat next to his Mistress. Diane gently kisses him. Slowly they cuddled. She lit a cigarette and offered him one as well. He took it and smoked it as she had told him, like a girl.

"Christopher, you belong to me, remember."

"Yes, Mistress."

"Good. Then, you are to go home today and tell your parents I have hired you to help with some remodeling in my house. Each day you are home for vacation you will be here. Is that clear?"

Chris exhaled through his red lips, crossing his booted legs like he had seen women do.

"Yes Mistress."

Diane smiled at his girlish posture.

"Oh yes. You are a fine student, how easily you see what you need to do. But, there is still much to learn. Yes, my slave, your real education is just beginning."


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