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My calculus professor always wore what my father called sturdy shoes. I was a naive 18-year-old and simply knew her as the teacher with the most spectacular ass. She also had a formidable rack and a nipped waist, but her ass was truly spectacular. However, her traditional footwear truly mesmerized me and made my cock achingly hard.

Her sturdy shoes were always so, so shiny. Sometimes — if I got lucky — when she stood close to me just right, I could see the reflection of her white underwear on the dark surface of her polished toe box.

Her humble clothes and matronly footwear did something for me. I’d rush home and fantasize about her as I jerked off many, many times — usually until I couldn’t come anymore.

After I moved in with Trudy, she immediately demanded to know my fantasies: What got me off? What did I like? What turned me on? What would make me come so hard I heard heavenly music?

For her, it was ropes and nipple clamps.

For me, it was stern matrons in sturdy shoes.

Trudy had sucked my cock, while I told her all about my memories. Throughout the blowjob, my girl made sure she cupped my balls and squeezed them gently. She had my shaft all the way down her throat when I told her about me stealing one of my professor’s shoes from her office closet and jerking off as I sniffed it.

Trudy sat back, wiped the corners of her lips daintily and said, “Well, I’m gonna take a shower and then we’re going to go shoe-shopping.”

“For real?” I asked in amazement.

“For real!” She smacked my knee enthusiastically, stood and stripped naked right there in the living room.

I hopped in the shower with her to make good time and then we were off to have a quick dinner out and buy some cock-hardening shoes.

After eating, we went to the local mall. Many of its stores had closed long ago, and nothing new had taken their place. But it still had an old-school shoe store that sold ugly uniform loafers for school students and very comfortable-looking footwear for unfashionable adults.

Trudy dragged me right to a selection of matronly heels. My cock got hard the moment she began to run her delicate fingers over the plain pumps. Her fingernails were painted electric orange, so they really contrasted with the muddy brown and black leather.

She picked up a Mary Jane style with buckled ankle straps, rounded toes and low heels. The brass buckle threatened to make me come in my pants.

Trudy caught the helpless look on my face and grinned. Wiggling one shoe above her head, she called out to the salesperson. “Can I try these in a nine?”

The woman gave a brisk nod and disappeared into the stockroom.

Trudy sat and toed off her black sneakers. She snagged a pair of tiny beige nylon footies from a nearby box and made a big show of slipping them on.

The saleswoman returned and handed over a box. Just then a bunch of people entered all at once, and the worker lost interest in me, my girlfriend and her homely shoes.

Trudy had dressed the part for the occasion: her plainest pleated skirt, her most dowdy blouse and an old cardigan sweater. She’d pulled her hair into a bun, and I’d fought the urge to throw myself at her feet and beg her to allow me to enter her body immediately.

She slid one foot into the brown shoe, testing the size, and then she carefully fastened the strap. It was excruciating to watch. The first shoe fit well, so she slipped into the second with flair.

I felt my pulse pounding in my temples as Trudy ran the rounded toe of the shoe up the inside of my thigh.

The saleswoman was busy hustling shoeboxes to the rush of customers.

What a lucky break for us, I thought.

My whole body felt electrified as Trudy edged the shoe closer to toward my crotch. My jeans were barely containing my raging hard-on, and my face felt so hot I thought my cheeks must look cherry red.

I noticed the saleswoman place boxes on the floor and quickly right herself. I pushed Trudy’s foot away as gently as I could and turned slightly to hide my erection as the woman rushed over to us.

“How are we doing?” she asked.

Trudy told her, “I’d also like to try on the black patent leather ones that were next to these, please.”

The woman glanced at the display shelf, gave a nod of acknowledgement and hurried through the swinging doors to the stockroom.

The patent leather ones almost reminded me of tap shoes — the ankle-strapped numbers made famous by actresses who danced and sang in ’50s movie musicals.

The saleswoman emerged, handed Trudy the shoes and added, “Flag me down if you need anything else. We have a bit of a crowd this evening.”

Trudy assured her she would.

Meanwhile, my cock was throbbing painfully.

The patent leather shoes made me so aroused I almost felt faint. Trudy slipped into them and walked across the store’s polished wooden floor. The heels had just enough height to enhance her ass, thrust out her tits and make her sway her hips from side to side as she strutted.

Before my dick exploded in my pants, I directed Trudy to the register.

“I’d like to pay for both pairs — the brown and the patent leather,” I said to the clerk.

Trudy was next to me, laughing softly. She clearly intended to wear the black patent leather pair out of the store. She put her sneakers in the empty box and placed both cartons on the counter.

We made it to my SUV, and I exhaled so loudly I sounded like I was deflating.

“You’re really worked up, aren’t you,” she stated matter-of-factly after we had climbed aboard.

She turned in the passenger seat, contorting herself to push the toe of her shoe to my button fly.

I moaned.

She hooked one foot onto the steering wheel and draped her other leg across my thighs. She waggled her foot playfully in my lap and said, “Get yourself off.”

We were parked way in the back of the mall’s vast parking lot. No vehicles or people were near us, but I was still nervous.

“Now?” I asked.

My body wanted her to say yes — and she did. How did I get so lucky?

I glanced around once more, saw no bystanders and fished out my cock. She kept posturing, wagging her feet this way and that as she modeled the delicious virgin patent leather shoes. I fixated on Trudy’s footwear as I jerked off. My fist moved so fast it was a blur on my aching member.

Gazing at the shoe on the wheel, I could see the barest reflection of myself in the shiny surface and detect the fragrance of brand-new patent leather.

I came with a grunt and a shudder.

Trudy laughed with devilish delight, then handed me some napkins from her purse to clean up and said, “Now, let’s go home and see about that other pair.”

I nodded, started the car with shaking hands and sped home. By the time we arrived, my cock was raring to go all over again. She was so incredibly sexy.

At home, Trudy made me wait for her in the kitchen. When she came down from the bedroom, she was dressed differently — but it was perfection. She’d put on a high-necked floral dress, another cardigan, seamed stockings and the new brown Mary Janes.

To my stunned delight, she also held a ruler, and her hair was still in its prim teacher’s bun.

I was standing but felt my knees buckle.

“You’ve been a very bad boy. Staring at my shoes. Making a mess,” she said sternly.

I nodded, not trusting my voice. The beautiful thing about Trudy is she goes all out.

She sat in a kitchen chair and patted her lap as she demanded, “Come on then. Take your punishment.”

My feet were leaden, but I managed to move them.

I went where she indicated, draping myself over her lap. My face pointed directly at her mesmerizing shoes.

The ruler snapped against my ass hard enough to startle me, and my whole body bucked.

Breaking character briefly, Trudy was struck with a case of the giggles. But she soon stifled her laughter. Once she got herself under control, she went back at me with the ruler.

Ten hard slaps against my ass had me squirming. Every swat was accented with a tap of her toe on the kitchen floor.

“Pants off,” she said.

I stood and got rid of my jeans and boxer briefs.

She twirled her finger and added, “Turn.”

I obeyed. Without warning, she swatted me four times on my bare ass with the ruler. I hissed and bounced on my toes. Then she turned me to face her, and her hot mouth engulfed my stiff dick. She sucked me hard and then soft, randomly alternating, so I never knew what was happening next.

Keeping my hands clasped behind my back, I tried to behave. But I blurted out, “I’m going to come! Oh, fuck. I’m going to come.”

She sat back, swatted my thigh with the ruler and barked, “Language!”

“Sorry!” I replied, feeling myself blush.

Next, Trudy slid to the floor and hiked up her dress. Beneath it, she was bare — aside from her thigh-high stockings. There were no panties in my way.

“Show me how sorry you are,” she said coolly.

I dropped to the floor and peppered her with kisses, starting at her feet. The shoes smelled strong as I kissed them. When I finally reached her pussy, I lapped at it until she grabbed a handful of my hair.

“Fuck me,” she ordered.

I climbed atop Trudy and nestled myself between her spread thighs. Plunging into her hot cunt made me gasp, but she gasped, too. I didn’t think she anticipated how excited this scenario would make her.

I pumped into her, savoring every wet slide into her blissful cunt. She squeezed her muscles around my dick. I groaned and struggled to keep from coming immediately.

She clutched my back and thrust up her hips to take me, and then she was coming. The blissful rippling of her wet velvet pussy thrillingly massaged my dick, and her sounds of release were music to my ears.

“Don’t you come yet!” she warned.

I stopped my movement, startled by her outburst.

“Don’t you come inside me. Save it for my shoes, bad boy.”

Her words nearly did me in. I quickly pulled free of her snatch, and she braced herself on her elbows to watch me jerk myself off. I spurted white jets of cream all over her pristine, matronly shoes. It was such a thrill, watching the pearlescent threads streak the brown leather.

I shuddered and shook until I was finally spent.

Trudy clearly had plenty to teach me, and I could tell her new shoes were going to be a lot of fucking fun.

" />

My Stunned Delight

Storyline

My calculus professor always wore what my father called sturdy shoes. I was a naive 18-year-old and simply knew her as the teacher with the most spectacular ass. She also had a formidable rack and a nipped waist, but her ass was truly spectacular. However, her traditional footwear truly mesmerized me and made my cock achingly hard.

Her sturdy shoes were always so, so shiny. Sometimes — if I got lucky — when she stood close to me just right, I could see the reflection of her white underwear on the dark surface of her polished toe box.

Her humble clothes and matronly footwear did something for me. I’d rush home and fantasize about her as I jerked off many, many times — usually until I couldn’t come anymore.

After I moved in with Trudy, she immediately demanded to know my fantasies: What got me off? What did I like? What turned me on? What would make me come so hard I heard heavenly music?

For her, it was ropes and nipple clamps.

For me, it was stern matrons in sturdy shoes.

Trudy had sucked my cock, while I told her all about my memories. Throughout the blowjob, my girl made sure she cupped my balls and squeezed them gently. She had my shaft all the way down her throat when I told her about me stealing one of my professor’s shoes from her office closet and jerking off as I sniffed it.

Trudy sat back, wiped the corners of her lips daintily and said, “Well, I’m gonna take a shower and then we’re going to go shoe-shopping.”

“For real?” I asked in amazement.

“For real!” She smacked my knee enthusiastically, stood and stripped naked right there in the living room.

I hopped in the shower with her to make good time and then we were off to have a quick dinner out and buy some cock-hardening shoes.

After eating, we went to the local mall. Many of its stores had closed long ago, and nothing new had taken their place. But it still had an old-school shoe store that sold ugly uniform loafers for school students and very comfortable-looking footwear for unfashionable adults.

Trudy dragged me right to a selection of matronly heels. My cock got hard the moment she began to run her delicate fingers over the plain pumps. Her fingernails were painted electric orange, so they really contrasted with the muddy brown and black leather.

She picked up a Mary Jane style with buckled ankle straps, rounded toes and low heels. The brass buckle threatened to make me come in my pants.

Trudy caught the helpless look on my face and grinned. Wiggling one shoe above her head, she called out to the salesperson. “Can I try these in a nine?”

The woman gave a brisk nod and disappeared into the stockroom.

Trudy sat and toed off her black sneakers. She snagged a pair of tiny beige nylon footies from a nearby box and made a big show of slipping them on.

The saleswoman returned and handed over a box. Just then a bunch of people entered all at once, and the worker lost interest in me, my girlfriend and her homely shoes.

Trudy had dressed the part for the occasion: her plainest pleated skirt, her most dowdy blouse and an old cardigan sweater. She’d pulled her hair into a bun, and I’d fought the urge to throw myself at her feet and beg her to allow me to enter her body immediately.

She slid one foot into the brown shoe, testing the size, and then she carefully fastened the strap. It was excruciating to watch. The first shoe fit well, so she slipped into the second with flair.

I felt my pulse pounding in my temples as Trudy ran the rounded toe of the shoe up the inside of my thigh.

The saleswoman was busy hustling shoeboxes to the rush of customers.

What a lucky break for us, I thought.

My whole body felt electrified as Trudy edged the shoe closer to toward my crotch. My jeans were barely containing my raging hard-on, and my face felt so hot I thought my cheeks must look cherry red.

I noticed the saleswoman place boxes on the floor and quickly right herself. I pushed Trudy’s foot away as gently as I could and turned slightly to hide my erection as the woman rushed over to us.

“How are we doing?” she asked.

Trudy told her, “I’d also like to try on the black patent leather ones that were next to these, please.”

The woman glanced at the display shelf, gave a nod of acknowledgement and hurried through the swinging doors to the stockroom.

The patent leather ones almost reminded me of tap shoes — the ankle-strapped numbers made famous by actresses who danced and sang in ’50s movie musicals.

The saleswoman emerged, handed Trudy the shoes and added, “Flag me down if you need anything else. We have a bit of a crowd this evening.”

Trudy assured her she would.

Meanwhile, my cock was throbbing painfully.

The patent leather shoes made me so aroused I almost felt faint. Trudy slipped into them and walked across the store’s polished wooden floor. The heels had just enough height to enhance her ass, thrust out her tits and make her sway her hips from side to side as she strutted.

Before my dick exploded in my pants, I directed Trudy to the register.

“I’d like to pay for both pairs — the brown and the patent leather,” I said to the clerk.

Trudy was next to me, laughing softly. She clearly intended to wear the black patent leather pair out of the store. She put her sneakers in the empty box and placed both cartons on the counter.

We made it to my SUV, and I exhaled so loudly I sounded like I was deflating.

“You’re really worked up, aren’t you,” she stated matter-of-factly after we had climbed aboard.

She turned in the passenger seat, contorting herself to push the toe of her shoe to my button fly.

I moaned.

She hooked one foot onto the steering wheel and draped her other leg across my thighs. She waggled her foot playfully in my lap and said, “Get yourself off.”

We were parked way in the back of the mall’s vast parking lot. No vehicles or people were near us, but I was still nervous.

“Now?” I asked.

My body wanted her to say yes — and she did. How did I get so lucky?

I glanced around once more, saw no bystanders and fished out my cock. She kept posturing, wagging her feet this way and that as she modeled the delicious virgin patent leather shoes. I fixated on Trudy’s footwear as I jerked off. My fist moved so fast it was a blur on my aching member.

Gazing at the shoe on the wheel, I could see the barest reflection of myself in the shiny surface and detect the fragrance of brand-new patent leather.

I came with a grunt and a shudder.

Trudy laughed with devilish delight, then handed me some napkins from her purse to clean up and said, “Now, let’s go home and see about that other pair.”

I nodded, started the car with shaking hands and sped home. By the time we arrived, my cock was raring to go all over again. She was so incredibly sexy.

At home, Trudy made me wait for her in the kitchen. When she came down from the bedroom, she was dressed differently — but it was perfection. She’d put on a high-necked floral dress, another cardigan, seamed stockings and the new brown Mary Janes.

To my stunned delight, she also held a ruler, and her hair was still in its prim teacher’s bun.

I was standing but felt my knees buckle.

“You’ve been a very bad boy. Staring at my shoes. Making a mess,” she said sternly.

I nodded, not trusting my voice. The beautiful thing about Trudy is she goes all out.

She sat in a kitchen chair and patted her lap as she demanded, “Come on then. Take your punishment.”

My feet were leaden, but I managed to move them.

I went where she indicated, draping myself over her lap. My face pointed directly at her mesmerizing shoes.

The ruler snapped against my ass hard enough to startle me, and my whole body bucked.

Breaking character briefly, Trudy was struck with a case of the giggles. But she soon stifled her laughter. Once she got herself under control, she went back at me with the ruler.

Ten hard slaps against my ass had me squirming. Every swat was accented with a tap of her toe on the kitchen floor.

“Pants off,” she said.

I stood and got rid of my jeans and boxer briefs.

She twirled her finger and added, “Turn.”

I obeyed. Without warning, she swatted me four times on my bare ass with the ruler. I hissed and bounced on my toes. Then she turned me to face her, and her hot mouth engulfed my stiff dick. She sucked me hard and then soft, randomly alternating, so I never knew what was happening next.

Keeping my hands clasped behind my back, I tried to behave. But I blurted out, “I’m going to come! Oh, fuck. I’m going to come.”

She sat back, swatted my thigh with the ruler and barked, “Language!”

“Sorry!” I replied, feeling myself blush.

Next, Trudy slid to the floor and hiked up her dress. Beneath it, she was bare — aside from her thigh-high stockings. There were no panties in my way.

“Show me how sorry you are,” she said coolly.

I dropped to the floor and peppered her with kisses, starting at her feet. The shoes smelled strong as I kissed them. When I finally reached her pussy, I lapped at it until she grabbed a handful of my hair.

“Fuck me,” she ordered.

I climbed atop Trudy and nestled myself between her spread thighs. Plunging into her hot cunt made me gasp, but she gasped, too. I didn’t think she anticipated how excited this scenario would make her.

I pumped into her, savoring every wet slide into her blissful cunt. She squeezed her muscles around my dick. I groaned and struggled to keep from coming immediately.

She clutched my back and thrust up her hips to take me, and then she was coming. The blissful rippling of her wet velvet pussy thrillingly massaged my dick, and her sounds of release were music to my ears.

“Don’t you come yet!” she warned.

I stopped my movement, startled by her outburst.

“Don’t you come inside me. Save it for my shoes, bad boy.”

Her words nearly did me in. I quickly pulled free of her snatch, and she braced herself on her elbows to watch me jerk myself off. I spurted white jets of cream all over her pristine, matronly shoes. It was such a thrill, watching the pearlescent threads streak the brown leather.

I shuddered and shook until I was finally spent.

Trudy clearly had plenty to teach me, and I could tell her new shoes were going to be a lot of fucking fun.

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