Miss De Stefano

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By ErrantKitten

Miss De Stefano laughed at me when I first undressed in front of her in our suite at the Hilton. I had gone to all this trouble, getting my beautiful executive secretary to come with me from work to a hotel room, it had taken so much cajoling, begging, gifts.

That’s right. The day I hired my secretary, she nicknamed me Poodle, and instructed me to call her Miss De Stefano, although she was twenty-four and I was fifty-six. It just worked that way.

They say that expectations are a resentment waiting to happen, but I really thought it would be better than what happened. Miss De Stefano just sat on the bed in her sexy turquoise mini dress that didn’t quite cover the tops of her magnificent thighs. Miss De Stefano had crossed her legs, letting one six-inch Blahnik heel dangle and she jutted out her big boobs protruding over the plunging neckline.

“Go ahead, Poodle, strip for me.” So I had undressed and stood there. I’m afraid I was cowering in front of her, my pudgy naked figure, and incredibly, Miss De Stefano had laughed at me, the big boss.

“Jesus, Poodle, you resemble Pop n’ Fresh.”

“Who?” I asked stupidly.

“You know, the Pillsbury Doughboy in the commercials.” Miss De Stefano laughed and her beautiful cleavage jiggled.

“You’re chubby and pale white, like Pop n’ Fresh, the Doughboy all you need is the chef’s hat.

My God and your penis is tiny, almost non-existent. I can’t believe I came up here to see that.” She laughed cruelly and I am afraid to say I blushed.

But her breasts heaved again, and my little cock got kind of excited. I was absolutely hypnotized.

I did try to assert myself, but it was difficult to look haughty, masculine and dignified in front of a fully dressed New Jersey Italian brunette in a tight turquoise dress, with glossy lips and a French manicure. And she was smoking, and occasionally flicking the ashes and sparks at my nipples.

Miss De Stefano reminded me of the tough, wise cracking girls I had gone to high school with.

Being in honours classes, I had not interacted with the blue-collar chicks much other than noticing the tight jeans they wore as they shimmied down the hall past us advanced placement nerds with our slide rules and pocket protectors.

These tough street girls, with their big hair, cracking their gum, smoking cigarettes and doing blow in the bathrooms…They’d arrive at school on the back of motorcycles or climbing out of psychedelic vans. They had a life I couldn’t even imagine.

Big, teased hair, just like Miss De Stefano. I wouldn’t have had much to do with girls like this, but I was writing a lot of papers for school and I had decided to take a course in shorthand so I could take notes faster, and also a typing course.

After some time I made friends with one of the girls, Roxanne, who got me first to tutor her in geometry and French.

And then Roxie just got me to do her papers for her, and occasionally to lend her money. Sometimes I would be doing Roxie’s history term report, and she would be making out with a recently paroled ex-convict in the corner of her living room.

Once or twice Roxie gave me a hand job, a quickie, when the ex-con wasn’t around, just so I’d keep coming back and doing her work for her. I was absolutely amazed by that girl, I really was.

And now darling Miss De Stefano was so much like Roxie! Now I was quivering naked in front of my fully clothed secretary.

“Here, let me see something.” Miss De Stefano pulled me over and toyed with my penis and began pulling out my pubic hair, a few tufts at a time. I winced, but stood still, I loved breathing in her scent.

“Now stand still, Poodle. This makes me hot, seeing how you’d look with no pubes, baby. You want to turn me on, don’t you?” Amazingly, when I was bald down there and still knock kneed in front of Miss De Stefano, she did look a little more interested.

“Aren’t you going to undress, Miss De Stefano?” I asked in a quavering voice. I couldn’t believe how my voice was trembling, but Miss De Stefano was so beautiful. Her satiny breasts tranquillized me as they heaved in the little cleavage dress.

Miss De Stefano ground her cigarette out on my left nipple and I squealed. “I want to pull a few more hairs out and look at this infantile dinky. What a small penis!”

I came even closer and Miss De Stefano took my little dick in her sexy hands, running a long nail up and down my quite excitable cock.

She tickled my balls and stroked my penis faster and faster, and I began shaking as if I would cum, and suddenly, Miss De Stefano burned the end of my dick with her cigarette.

“What are you doing?” I asked, in an agonized tone.

“Just need to calm you down, Poodle, but this really is a tiny little thing. I wish I had a microscope.”

“Can you even pee standing up, Poodle? I’d think you would need to sit down like the ladies with a clitty like this one.” Miss De Stefano asked this in a mock concerned tone.

Miss De Stefano rubbed the top of my swelling penis. Her full lips curled into as mile as she looked down at my little wee-wee, encased in her lovely fingers.

There seemed to be no lust in Miss De Stefano’s lovely eyes, but I knew she would stay interested, as I’d bought her a Hermes scarf, a tennis bracelet and a diamond ring. All this, just to get her to the hotel room, without suing her boss for sexual harassment.

As Miss De Stefano rubbed and stimulated my small wiener, I Wondered if she would ever remove any of her clothes, even her shoes.

I was so hot to see Miss De Stefano’s naked body; the most I’d seen so far was at the Maui corporate retreat, where Miss De Stefano had worn a variety of tiny bikinis while playing extensive volleyball with younger members of the corporate staff.

I confess that several times I listened outside her bungalow on that retreat as she fucked young account executives, but my wife had been alone, and I had not had the nerve to ask Miss De Stefano for a little fun for myself at that time.

Twice I had stolen my secretary’s panties from the laundry at the retreat, and I’d masturbated sniffing them, but the trail had really come when I had watched Miss De Stefano play volleyball. She had some moves, that girl.

I thought I was just going through a childish crush but…

But I knew then, watching Miss De Stefano’s cantaloupe sized breasts bouncing in the strained swimsuit cups that I had to find a way to get in her good graces, and then into her bed.

It had taken another ten months of lunches, dinners, gifts and favours and now I was in the hotel with her, but unfortunately I was naked and Miss De Stefano wasn’t.

I decided to stop being timed and reached for her, but again that apparently was a mistake.

As I grabbed Miss De Stefano’s breast, Miss De Stefano let go of my penis and slapped me with a roundhouse whack as hard as she could. Right across my face, and nearly at the same time her lovely leg came up and kneed me in the balls.

I fell over, almost blacking out.

“Who the fuck do you think you are, you total asshole?” Miss De Stefano screamed as she stood up over my prone form, clenching her little fists.

I was still lying on the floor, dazed as Miss De Stefano walked up and stomped the glans of my penis into the floor with her high heel.

“And to think you wanted to fuck me with this Shrimpy little worm!”

My penis was being ground into the hard floor with Miss De Stefano’s six-inch heel as she screamed at me at the top of her lungs.

Suddenly there was a knock at the door, and mindless of my nudity, Miss De Stefano stalked over to the door (blessedly taking her heel off my welted penis) and there was a bellhop out in the hall.

“Senora, the management asked that you keep it down in here.”

“What’s your name?” Inquired Miss De Stefano in a seductive voice.

“I’m Pedro.”

Miss De Stefano brought the bell boy into the room and snapped her fingers at me.

“Get on your knees, Poodle.” She looked up into the eyes of the now blushing bellhop who was muttering ‘Aye Caramba’ under his breath.

“Pedro, look at this man’s silly little penis and tell me, don’t you think it’s pretty small?”

And the little spic bastard laughed. There I was, Vice President and Head of Mergers and Acquisition at Pembroke & Pettibone, kneeling naked while a South of the Border probably illegal immigrant bellhop laughed at my little cock.

I rose. “This is intolerable, Miss De Stefano. You…”

But as I spoke, Miss De Stefano turned to Pedro. “Do you have a belt? A strong leather belt that I can use, Pedro? All Poodle has is his faggy suspenders.”

The grinning young hotel employee gave Miss De Stefano his big leather belt that had a huge metal skull as the buckle. He must be in some biker gang, I thought.

Miss De Stefano spun on me, swinging the looped belt, which smacked my shoulder and then before I could react, she swung it again, whacking me on the cock and balls.

WHACK! WHACK! Doubled over from the pain in my nuts, I was barely cognizant as she slapped my testicles again with the heavy skull belt buckle. Miss De Stefano really could wield that thing.

I doubled over from the intense pain in my testicles, and Miss De Stefano grabbed me by the left ear and led me to the bed.

As the bellhop watched avidly, (these weird gringos!) Miss De Stefano took me over her knee sitting on the bed and began whacking my naked bottom. WHACK! WHACK! WHACK! WHACK!

I tried to rise, but Miss De Stefano had my arm trapped behind my back and she whipped me hard and I gave up the struggle and began wailing.

The bellhop started putting his finger to his lips, and Miss De Stefano nodded her head, understanding. “Do you have a hanky, Pedro? Just stuff it in his mouth so Poodle doesn’t disturb the other guests.”

Incredibly, the little Mex fucker shoved a cologne soaked neckerchief into my screaming pie hole and I almost vomited.

Miss De Stefano commenced whipping me with the belt, and I screamed more. Although of course I was muzzled now, with the nauseating handkerchief. I couldn’t believe this was happening. But it was reminiscent.


My mother, a strident shapely redhead had punished me often by whipping my bare bottom with a saucepan, until I had escaped to college.

Mother had been terribly strict. I remember throwing a fit because I had invited a couple of the sexiest hotties from the typing class over, Roxie and Danielle. I wanted them to watch a movie with me one Friday night.

Mother had informed them that my bedtime was seven-thirty, and I was about to get an enema as well. “They must leave,” Mother said.

I had begged and pleaded in front of the amused girls, telling Mother that eighteen was too old for a bedtime, especially seven-thirty on a Friday night.

Finally, Mother had calmly grabbed me, pulling down my pants and going at it on my bare buttocks with her trusty saucepan until I cried in misery.

Then she had made me get into my pink footie pajamas with the snap up bottom and tell the girls before I went to get my enema and go to bed, sobbing in humiliation.

I had never been able to face the girls in the typing class again. I was terribly humiliated as the story had gotten all over school. And now it was happening again, thirty years later!

Now I was being thrashed by my secretary in front of a barrio Hispanic. Finally Miss De Stefano let me up and I spat out the smelly handkerchief, and was almost on the verge of puking from the damn cologne.


I stood there and cried, and watched in sadness as Miss De Stefano walked over to Pedro and gave him a big kiss. “Show me your penis, Pedro” she murmured. “I need to see what a real man looks like for a change.” Miss De Stefano kissed Pedro several more times and the boy pulled out his long brown cock.

Miss De Stefano stroked Pedro’s big penis with her long nails and smirked at me. “See, that’s a real dick not like your sad little member, Poodle.”

I stared at my feet. How could it get worse? But indeed, it did.

“I think you should suck Pedro’s penis to show obeisance, and worship, right now.”

I gaped at this woman who I’d begged and bribed to come to the hotel room so I could make love to her. True, my cock was lengthening and hardening as I contemplated my degradation, but this was going way too far.

There was another knock on the door, and Miss De Stefano opened it up to admit Pedro’s older brother Pablo, and as I watched in amazement, within moments, she had Pablo’s dick out, too.

The two bellhops were just amazed by how things were going here in Room 402. But I would have no more of it and told Miss De Stefano to go to hell, that I was leaving this ridiculous, humiliating situation.

But Miss De Stefano grabbed Pedro’s belt and came up to me. WHACK! The huge skull buckle hit my hard cock and balls and I doubled over in pain.

“You are a pitiful limp dicked little pussy and I just ordered you to suck off two better men and you had damn well better do it!”

Miss De Stefano swung the belt across my dick again. Incredibly, this time I just stood there. I took it as my dick seemed to stay hard even behind the evil whipping.

Finally, as if in a dream, I dropped to my knees and I sucked Pedro’s dick, as Pablo slammed his dick in my anus. I cried in submissive misery around Pedro’s smelly penis, but was completely submissive, even when Pablo ordered me to suck my shit off his dick and give him another BJ.

After the cocksucking and sodomy were over, and my mouth and ass were full of Mexican cum and my own vices, I watched as both bellhops went to the bed with Miss De Stefano, undressing her and hitting every hole.

They fucked like rabbits for over an hour as I watched in total fascination. And of course I loved checking out Miss De Stefano’s beautiful body.

Finally, Miss De Stefano rose and gave the boys a big tip from my wallet and they left. I was still kneeling and staring at Miss De Stefano’s gorgeous figure. Those pink areolas had been just incredible!

Miss De Stefano looked at me and smiled. “You poor baby. I won’t let you fuck me, but if you like you can lick me all over, and eat the semen out of my pussy and asshole. And of course of my breasts, stomach and legs, where they jerked off on me one last time with their manly sperm.”

I went at this task with vigour, jumping on the bed and ended up bringing Miss De Stefano to several orgasms while I was at it. I kissed Miss De Stefano’s beautiful, satiny breasts with ardour and gave her lots of hickeys.

Finally Miss De Stefano told me that I’d been great and she instructed me to lie on the floor as she climbed up on the chair. She raked her sharp red toenails up and down my stiff cock until I had the best orgasm of my life. Of course after that I submissively licked Miss De Stefano’s toes clean.

After I helped Miss De Stefano dress, she told me that I was a good boy. “You have to understand, Poodle, I don’t fuck children. You have the penis of a toddler, and your attitude is incredibly egotistical and childish. That’s why you need the regular attentions of a belt or perhaps a bullwhip.”

“See how your attitude changed after I gave you a few licks? You sucked Pedro and Pablo quite expertly, their big and beautiful penises, and you gave me a nice massage with your hands and tongue. You have real potential, honey.”

I had to agree, and I bent down to kiss Miss De Stefano’s feet once more.

The next day at the office, Miss De Stefano showed up looking just gorgeous in a bright pink dress, with even more cleavage and frilly bra peeking out. But she seemed not to remember what had happened the day before.

I followed her around like the office like a puppy, ignoring work and staring at her with pain in my eyes. Finally, my secretary became quite annoyed with me.

Grabbing me by the ear, Miss De Stefano dragged me into my own little executive bathroom and she sat down on the toilet.

“What the hell is wrong with you, Poodle?” Miss De Stefano demanded.

“I made the mistake of giving you a little action in the hotel yesterday. And now you are stalking me. You are out of your mind.”

I bit my lip in the narrow little lavatory, standing over her, and tears came into my eyes. “But Miss De Stefano, I just really enjoyed yesterday, so much and I want you to be my girlfriend. I’ll leave my wife and kids, I swear.”

But now the tears were welling in my eyes and my knees were knocking. I was terrified that Miss De Stefano would just never fool around with me again.

It was true that getting whipped was a bit of a thrill, and sucking off Pedro and Pablo, although disgusting was a small price to pay for kissing Miss De Stefano’s beautiful pink nipples and saucy clitoris.

But Miss De Stefano seemed quite annoyed. “You are such a disgusting whiner, Poodle. I would never have a sissy like you for a boyfriend.” Miss De Stefano was staring up at me from her perch on the toilet seat, and I confess I just stared into her incredible cleavage.

“You remind me of my twin sister, Albertine, she whined so much that my mother had to constantly whip her with a hairbrush. Sometimes Momma would put Albertine in diapers when she threw an immature fit, even when Albertine was in her twenties.

Now, Albertine lives down the block from me and whenever she calls me up and whines, I go down there with my deceased mother’s hairbrush and take my twin sister over my knee and whip her till she cries.”

I became somewhat aroused by this story. I had seen Albertine in the office a few times, and she was quite gorgeous as well…

But now Miss De Stefano was talking again. “I was afraid I’d get a lot of crap from you today, so I brought Momma’s hairbrush in my purse.”

Oh, Jesus, I thought. I turned to flee the bathroom, but Miss De Stefano had locked the door. I felt her small delicate hand grab my crotch squeezing my testicles through my Armani trousers until my knees buckled.

Miss De Stefano turned me around and I saw the deadly big wooden hairbrush in her hand, the biggest I had ever seen. “Miss De Stefano I don’t want—”

But suddenly I was flashbacking. My mother was pulling my pants down in the market after I’d had a tantrum. Mother whipped my bare buttocks with the hairbrush, her disobedient eighteen year old, and the other patrons watched approvingly.

And now it was happening again. I had less control over my clerical assistant than I had over my domineering mother.

I struggled with my seated secretary, who then ripped off my suspenders and tied my shirt tails in a loop around my belly…Then she dragged my pants and my tighty-whiteys to my knees, and of course pulled my left hand behind my back and threw me across her stockinged knees.

After a whipping that made me scream like a hysterical ballerina, Miss De Stefano puts me in adult diapers and locked the door to the office while I sobbed. Later we went to the hotel again and she called up Pedro and Pablo. I am happy, but confused. Oh well!

The End.


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