Mistress Besame

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Humiliated by his law-school classmate!
1.1k words
3.65
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Part 1 of the 24 part series

Updated 06/07/2023
Created 01/18/2016
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"Okay, hold still." Besame grinned at Wilton, and leaned over and lightly touched the lit cigarette against Wilton's hard cock.

Wilton tried desperately to hold still. God, she's so hot, with that spiky green hair, and the little T-shirt that looks like it's painted on. The burning ember grazed his penis, and Wilton bit his tongue to keep from screaming.

Besame smiled. "See? I might fuck you if you can learn not to be such a little wimp. If you can keep holding still, and not show a lot of pain..."

But then, from her sitting position, Besame's right leg shot out and kicked poor Wilton in the nuts, and he fell over, screaming. Besame put her cigarette in an ashtray and examined her magenta nails.

"See" she said boredly. "That's what I'm talking about. You just...your wimpiness seeps through every time, Wilton."

Gasping on the floor, Wilton wondered why he put up with this. And was it worth it, just to date a girl like Besame?

Besame nudged him with her heel. She jiggled her tits at Wilton as he looked blearily up at her from where he was writhing on the floor.

"You want these, right? You gotta earn it. Get the fuck up."

And of course, his cock was stiffening once more. It was sad. Wilton's fiancée, Gwyneth, was a former model and so very devoted to him, but he couldn't seem to break his Besame habit to save his life.

Wilton still hadn't risen, so Besame used her high heel to poke into the glans of Wilton's cock. She pushed it in, while puffing hard on the cigarette and looking down at him, mirthfully.

"Now are you going to cry like a little bitch?" Besame asked, giggling. "It's so attractive when you act like a Betsy-Wetsy doll. Crying, peeing yourself-"

"That only happened once." Wilton muttered. It was true. Once Besame had been teasing him on the train, they were sitting closely together and then suddenly she'd grabbed him through his pants and squeezed his balls, and he'd wet himself.

Now he tried to lie still as she ground his penis into the hardwood floor.

"That's right. Try to be a man, Wilton. You're a disappointment to us all, women everywhere, but I am going to try to change that."

But as reassuringly as she spoke, Besame pushed her spike heel harder into his penis, and it felt as if it was being drilled with a jack-hammer.

At the same time it was so exciting. Here he was, naked as the day he was born, letting a fully clothed punk rock girl torture his poor schlong. And he would try so hard not to cry, but she wouldn't make it easy.

Besame ground a little more, and although Wilton didn't cry out, he began tearing up, and she laughed and pulled her foot away. "Now get up, I am so bore d with this."

"You're bored?" How could that be, Wilton thought as he rose dizzily. He wondered if he should put witch hazel on his penis.

"Yeah. I have another man in my life, and he is so much tougher than you. I touched the tip of his dick with a steam iron, and he just squealed a little bit. Last winter I threatened to shove a fireplace poker up his ass, and he almost fainted, but not quite."

Oh, how I want to fuck her, Wilton thought, staring at her gorgeous legs. From time to time, Besame had allowed Wilton to give her full bodied massages, and he'd loved shaving her legs and rubbing cream on them.

"You think you want to fuck me, right?" It was as if she'd read his mind. "But you don't really want that. You like it that I abuse you. Who else would get in a situation like this one?"

Wilton looked down at the floor sadly. Yes, it was true. And he'd been so good to her! Wilton had bought Besame a diamond locket last year, and he'd taken her to Paris, where she'd fucked everyone else but insisted on a separate room in the hotel.

Poor Wilton, he'd had to sit in his room and listen to the bumping and moaning in the next room, Besame's screams of passion and the French asshole's howls of pleasure...

He'd barely spoken to her on the flight home...

He really was a pussy-boy!

Besame stroked her chin meditatively. Wilton tensed, wondering if she was going to kick him again. "Remember when we met in law school?" she asked.

Yes. There was a co-ed dorm, and she'd caught Wilton stealing panties out of her laundry bag. She didn't even know him, and she'd pulled his pants down in front of everyone in the dryer room and she'd whipped him with her sneaker.

Then, he'd confessed to her (as he was writing a paper for her) that during college, he'd lived with a maiden aunt, who had gone over his academic work and had punished him for laziness by making poor Wilton wear a plaid gingham dress like Dorothy wore in the "Wizard of Oz" and jump rope in the front yard!

"That must have been a drag for you." Besame had said. "What, was your aunt paying for college, was that why you were stuck there?"

And of course that wasn't why. Wilton had been on a full scholarship and had a trust fund besides, but Aunt Imogene had been good for him, and had kept him from slothfulness.

Sometimes Aunt Imogene had tied the then 20 year old Wilton down on the bed naked and had shoved habaneras peppers, horrible stinging things, up his anus until he'd bawled for a relief.

But he'd graduated from college with honors...he'd buried Aunt Imogene the summer before law school, and then he'd met Besame.

Several times since graduation, he'd tried to escape his weird relationship with this girl that wouldn't sleep with him, but he kept going back. They both practiced law in the same city...

Well, Besame didn't really practice law. She was a clerk for a Circuit Court judge, and she told Wilton that she liked to "pound old Marv's nuts with his own gavel" So how much work could that be?

"So today I went and bought some peppers." Besame smiled. "I know you can't have too much um, drama since you have to meet your precious fiancée later, but bend over and spread your cheeks, I want to get your attention..."

As Wilton sighed and bent over, he realized two things...

First, he'd probably never marry Gwyneth or anyone else.

And secondly, Besame would never marry him. And that was okay!

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