Lady Esolen

Esolen smiled at Claude. She shook her short dark hair. It was a bob, easy to control, but quite thick, and a bit curly. Claude stood in front of her, weeping slightly, and holding the thick leather strap.

"Claude, we talked about this." Esolen's soft voice resonated. Esolen never raised her voice. "There are rules and consequences. When I moved in with you, this place was a sty, and sometimes you need reminders so it doesn't return to that condition."

Claude bit his lip. He was quite a bit older than Esolen the sort of fellow that used to be called a "silver fox". A television executive, now retired, he was pleasant to live with.

Certainly Esolen didn't love him, and she sought many other beds, but it was a bit of a living, Claude compensated her for her company, and in a way he was so different from fickle boys, he had great stories and a good sense of humor (perhaps not just now) and had taught her a bit about the world.

But he was a naughty boy at heart!

"I-I just left a little stack of bills on the floor, Esolen." Claude said, his eyes pleading. Esolen could see Claude's crotch bulging, though.

"I know, honey." Esolen crossed her long, pretty legs. Esolen was clad in a demure if short skirt and a flowered peasant shirt. "But that's the way it starts, isn't it?"

"Y-yes, I-"

Esolen unbuttoned her shirt. "You want the rewards, of course. Don't you want to look at this?" Esolen reached into her shirt and pulled out a plump breast, and as always, Claude's eyes bugged out.

Esolen's fingers played with her rose colored nipple. "I know you'd like to lick and kiss it, and we're just not there yet in our relationship."

"B-but it's been eighteen months!"

"Yes. I might let you pound your puddie and look at my boobies after we deal with the business of the messy room."

"It was just a stack of bills!"

Esolen didn't raise her voice, but it did turn steely. "I've had enough of this." She put her breast back and buttoned up the shirt. Claude's face fell.

"Give me the strap. Right now."

Claude, beginning to weep, handed Esolen the thick leather strap.

"God, you're such a baby. You can't just take a little correction." Esolen shook her head. "My father used bigger straps like this on me, for just being late to the breakfast table, and I learned respect."

Actually this was complete bullshit. Esolen's parents were adoring Freudian therapists, and everyone had adored Esolen from birth, and why not?

Porcelain skin, and big eyes...full lips, and a minx-like personality. But she loved pretending she'd risen from abusive, blue-collar origins.

Esolen frowned portentously. "Now take your pants down and lie across the arm of the couch." She toyed with the leather strap, almost lovingly. "Go on, I don't have all day."

Claude shook his head, but seeing Esolen refusing to give in, he shuffled over to the couch and undid his pants and pulled them down, following with his jockey shorts.

Esolen got up and walked to him. "Now we're going to see what being slob brings you, won't we?"

Esolen raised and brought down the strap twelve times. Claude bit on a couch cushion to keep from screaming (loud noises irritated Esolen) but it wasn't easy. His buttocks felt like hamburger now.

Now he rose and was weeping profusely. Through bleary tears he looked at his roommate, who he paid five thousand dollars a month to be "kept in line."

God, she's beautiful, Claude thought. She keeps her lips rouged in burgundy, and goes out of her way to be attractive.

She makes wonderful food, and knows a lot about museums and culture. Sometimes I wish she'd marry me, but twenty-six to my sixty years is near to impossible...

And oh, how my butt hurts!

Esolen opened her arms and Claude went in for a hug, and he sobbed on her shoulder.

"There there, darling. Mommie doesn't like to have to hurt you, but now you're learning, aren't you? Baby is going to try harder, right?"

Claude felt Esolen's hand reach down and toy with his burgeoning penis. She rubbed and pulled it as she whispered in his ear, and then Claude felt her long tongue licking around his neck.

It wasn't always this way. Last week, Esolen had told Claude that she found his penis offensive and she'd made him stroke to erection and she'd poked it with a fork and then swatted it hard with a composer's wand that had belonged to Claude's late father.

By the end of three minutes, Claude had fallen to his knees, weeping, and Esolen had ordered him to stand again, and she'd cuffed his hands so he couldn't touch his penis.

But then she'd put his hot, damaged dick between her breasts and she'd pushed them against it, soft, cool mammaries, and it had been all worth it, right?

Esolen smiled as she let Claude lean in to her, now. She was only five foot five to Claude's six feet, and she had to reach up her left arm to hold him around the neck, and of course her right hand was busy twiddling his writhing snake.

Esolen jerked Claude's penis until it was on the verge of exploding, and she smiled to herself as she felt Claude tense. He was too well trained to make a mess in her hand. A few weeks ago, Esolen had been playing with Claude's cock as he got out of the shower and he'd had an accident all over her blouse.

Later he'd told her he didn't even enjoy it, since she let go of his penis immediately, and began screaming at him at the time...

Then she'd hung him from the garage ceiling and shot BBs at his cock with an air rifle he'd had as a youth.

So now he was trying desperately not to get too enthralled, to go overboard.

Later, if he was a good boy, she might let him jack off as she rolled her breasts in front of him.

Claude always looked so funny, kneeling naked on the floor, pulling and rubbing his sad little member, and you could tell his mouth just drooled to be able to kiss her pretty nipples. How he longed for that!

But that wasn't allowed. Claude wasn't allowed in her bedroom and Esolen had taken over the master bedroom when she moved in.

Esolen didn't even go to bed till about eleven, usually, unless she went out, but every night at seven-thirty, Claude had to put on his pajamas and come in and kiss her good night, and go to bed early.

It was good for him, and gave Esolen some time to herself. If Claude had especially annoyed Esolen, sometimes she would put him in diapers and lock him in the "Nursery" which was a room with a big crib.

There was a big rubber enema bag in there, and other equipment to make Claude regret his sins.

Esolen had had other living arrangements that had been of even stricter terms.

She'd lived with a female airline pilot who had slept in a small dog crate at the end of Esolen's bed, in the pilot's house, of course.

Esolen had also known a Lutheran minister, who she kept in pierced chastity, but occasionally attached the metal loop in his dick to a chain on the basement floor and made him stay down there until she felt he'd learned his lesson.

Now, Claude was trying to pull away slightly, as his penis was quivering and about to release. Esolen kept him tightly close to her. She rubbed harder and faster.

"What's wrong, my little prince?" Esolen crooned. "Don't you wish you could cum like other men do? Fuck me hard and show me what;s what? I know you used to be quite the cocksman."

She rubbed faster and blew in his ear.

"What was it, four ex-wives, dozens of secretaries and interns. It's a good thing you retired before the #Metoo movement came, isn't it?"

Esolen tickled the underside of Claude's cock.

"But now you're just a poor little sissy, the one who had to take violin lessons while the other boys were playing ball...maybe I can remind you of this more.

Perhaps tonight I'll have you put on the little Shirley Temple dress, and you can service the young fellow who comes to mow our lawn...

You belong on your knees, getting your mouth violated, don't you? Unlike a real man."

As Claude moaned and shot into Esolen's hand, she jumped away and backhanded him across the face. But Claude's cock was stiff even after it was empty!