Little Dickie Ch. 03

Inge's hair was long and straight, extending a little bit past her shoulders. Its natural color was a breathtaking hue of dark blonde and light brown. It was parted on the side, in a quasi-man's style. Her face features were angular, her make-up perfect. She was beyond elegant, she was beyond sexual; she was mouth-watering. "Jenn knows how to pick them," Jane told Clem, who readily agreed. She was wasting her beauty doing what she does, thought the Empress, until she found out how profitable her business was, but she could have married a billionaire. But maybe she was married to one; for all Jane knew, maybe a rich man had used her services and fell head-over-heels in love. Maybe Inge did what she did for kicks, while her wealthy benefactor peeped in voyeuristic ecstasy. Stranger things have happened.

What do dommes do for sexual release? Most of their customers are middle-aged or older, with unattractive, overweight bodies and thinning hair. It's rare to find a sub like Marty Montana. Jane guessed that Inge must get off on the act of subjugation itself. "She's the Rolls-Royce of mistresses," Jenn said. Inge had provided an itinerary of the training, which Jenn dutifully passed on:

Day one

1. Toe sucking
2. Over-the-knee spanking
3. Cock and ball torture
4. Masturbation

Day two

1. Ball busting
2. Cunt licking
3. Pegging
4. Masturbation

Day three

1. How to dress and undress a woman
2. Watch me fuck my boyfriend
3. Cock-sucking and anal intercourse with boyfriend

Day four

1. Prove he is a man by being able to fuck a woman

The latter was no sure thing, Jenn explained, because if Inge did too good a job, Little Dickie might be too traumatized to maintain an erection inside a pussy. "Remember that wuss, I think his name was Tomahawk Tom; he couldn't fuck, remember? He got all wobbly." Nobody wanted Dickie to end up like that, so he would need to be tested while the memory of fucking girls was still fresh, hence the need for day four. For much of his training he would be clamped, with the chastity device being removed only for scheduled masturbation and sex acts. But if Dickie proved to be a man; that is to say, a chick-with-a-dick, the training would be worth every penny. Jane could almost envision him as her houseboy, living in Herman's old bedroom, leaving the house only to appear in pornography shoots. But part of Dickie's appeal was his rambunctiousness; take that away and one might take away the part of him that was the most engaging, so she'd take a wait-and-see approach. She could live without a houseboy, but Arlene had Redwood Jim, Marlow had Koh, and if Herman successfully wormed his way into Connie's house, Jane would feel left behind.

She almost choked when she saw the ten-thousand dollar price-tag, but she could afford to overreact, seeing how deep her husband's pockets were. The moment of truth would, obviously, be day four, the day of Dickie's final exam. "Tell her there's an extra thousand in it for her, if the little bastard proves he's a man." Dickie would still be a Boner Boy regardless, because even if his penis ended up suffering from pussy-fright, it was something she could work into the scripts. In fact, the more she thought about it, pussy-fright might be a good thing.

****

Inge sat in front of her vanity mirror, touching-up her eyebrows. She was freshly showered and her hair smelled like violets. Makeup applied, she stood up, removed her robe, went to her closet and stared at her clothes. She liked to wear matching bra and panty sets, and she had already selected ones of silk that were satiny-smooth and crimson in color. Her panties were thongs, and once seeing the dress she chose, one immediately knew why. It was a lacy, cream-colored advertisement for classiness, sexiness and eroticism. It was so tight it seemed to be painted on her, which on a fat-free frame, is remarkable. The dress was long-sleeved, and the sleeves were as tight as the dress itself. Long sleeves usually led to upskirts, so claimed Herman, but it was not so in this instance. The dress was made of delicate material, yet it was opaque; one could not see through it, much to a pervert's consternation. The hem, obviously, was mini in the extreme, and had her butt cheeks been fuller it might have posed a problem, but the leanness of her upper legs, along with the thong, provided just enough cover. Yet, it remained so tempting, people like Herman would not be able to turn away, even knowing there'd be no panty-flashing.

When staring at her crotch one could see a light-gray liner that, in two instances, was visible below the hemline. Jane assumed this was a fashion faux pas, but she tracked down the dress online and saw that the liner was meant to show the way that it did. "Even I wouldn't pay that much for a dress," Jane harrumphed, afterwards, "but I got to say...shit, I'd be her fucking slave in a fucking heart-beat." But Inge's beauty and elegance, and her glamour, hinted at trouble too. This was a women so sexy that she could castrate your nuts and you'd still thank her. "This is what a fucking domme is supposed to look like," claimed the Porn Empress, and if Inge was willing, Jane wouldn't mind showing her the pleasures that can be had from a state-of-the-art, Japanese vibrator; a vibrator so good that Hideki had since bought the company!

Inge admired herself in a full-length mirror, smoothing over the dress. The beauty of the liner was that the dress wouldn't ride up on her. Inge had no time for upskirts; she didn't like showing them, nor did he care for the men who feasted on them. The dress sent a not-so-subtle message, which was that goddesses like her existed, and she might be available, but if you failed her, if you disappointed her, you'd pay for it dearly. That dichotomy contributed to her appeal. In the months that followed, Ivan Beatoffsky would boast on the blog that he watched her scenes over and over again, hoping for a different result. A dress couldn't be that short, and Inge couldn't move around the way she did without an upskirt, could she? Damn, it was frustrating; it was pervert hell.

"You'll be okay, Dickie," Jane reassured, on the fateful morning. The itinerary had built-in masturbation breaks and, "look, you'll get to fuck her on the last day. How sweet is that?" No mention was made of it being a test to see whether he could still perform, because why give him unnecessary stress?

****

Dan stood tall, if a little uneasily. She had already kicked him in the balls a few times, practicing for her next Boner Boy scene, she said, and now Connie held in her hand a wooden paddle that was about the length of ruler. However, and unfortunately for him, the paddle was about double the width of a ruler, so he knew there'd be a lot of pain, depending on how much she got off on the violence. He saw how hard she had spanked Little Dickie, witnessing a vicious streak he didn't know she had. It had been bottled up pretty good, and must have gotten unleashed by her role in Boner Boys. He enjoyed seeing this side of her, but he could do without the pain.

Connie rubbed Dan's butt. His hands were clasped firmly behind his neck, as instructed, or demanded, depending the point-of-view. His testicles were reddened and tender, but that didn't stop her from tapping their underside with the paddle. All things considered, he'd rather feel the sting on his firm cheeks than on his manhood. "I'm a fair woman," she said. "You got a choice." She either spank him as hard as she could, or she could cut him some slack. However, if he opted for hard, she'd stroke his cock as she paddled.

Dan took the path of least resistance. "Whatever gets your hand on my dick is what I choose." And why wouldn't he? Connie's hand was known to send men halfway to the moon, and as soon as it made contact with his dong it began to respond, despite having already smacked him twice, one on each cheek. But the power of her hand outweighed the power of the paddle. How would it feel, she wondered, if he got smacked while she was stroking him, so why not find out? Her hand was so warm and tender, so caressing and sensual, it overrode the pain, and her clenched hand felt iron in its grip. A true dominatrix would be insulted by a boner under such circumstances, but Connie wasn't a true domme. She was just a woman exploring the outer boundaries of her sensuality. Dan had always thought of her as just a size-queen, but now he saw her for what she really was; a major-league, genuine slut. And if that didn't give his bone a thrill, nothing would.

Connie kept paddling, and each whack grew in intensity. Her breathing got heavier, as did his yelps and grimaces. "I ain't stopping until you cum," she warned, so now the pressure was all on him. But there was another kind of pressure, the kind Connie exerted via her wanking and, once again, the power of the hand proved superior to that of the paddle. For the second time today Connie's hand was drenched with Dan's spunk. His ass was as red as his balls, but the successful milking spoke volumes. She waved the paddle under his chin. "Listen, mister. You're gonna fuck me, and you' fuck me good...or else." Dan wasn't concerned with 'or else'. His dick had never failed him before, and he thought he performed admirably; yet, he got sated before she did - she demanded more. What a woman, he thought. Dan followed her hungry-eyes, saw the vibrator, and using it as an aid, made the descent into the canyon to see whether his oral skills were still sharp.

It was déjà vu all over again, as the blowhole between her legs spewed forth a gusher that saturated the face of a pliant male. But it only made Dan's grin seem goofier. "Thank you," she panted. "I needed that."

"The pleasure was all mine."

****

Jovi was out banging Olivia, so it was just Koh and Clem in the house when Inge arrived. Jenn and Marty had accompanied her. "You know the drill, Marty," Jane said, and he did, so he quickly stripped. But nobody was watching the beefcake; all eyes were on the tall goddess, who commanded the room simply by her presence. Her shoes were anklets, a similar cream-color as the dress, and the heels added two inches to her height. She even towered over the formidable Mister Montana. Women know when they have met their superior, and Jane was in awe. The two nude men on the couch were in awe too, Koh wishing that he could trade places with Dickie. But Marlow's houseboy at least knew what his next masturbation fantasy would be.

Dickie was ordered to stand. "Don't look at me," she barked. But where should he look? Inge grabbed him by the scruff of the neck. "Don't get wise with me...you're pathetic," and she tossed him aside. The room grow quiet. I got to get this on film, thought Jane.

Dommes seemed to attract men with small penises, for nothing brought shame and humiliation quicker than a hot woman laughing at a ridiculously small package. But Inge took the high ground; she had four days to ridicule, so why do it in front of others? "Okay, little subbie, let's get this started." She took out a chastity clamp from her purse. "Put this on." Dickie looked at Jane for support, he looked at Jenn, and he looked at Koh and Marty, but they were powerless. The clamp was made of clear-colored plastic, so the penis was entirely visible inside it, but similar to the one Jane used on Herman, it allowed absolutely no room for growth. Inge knelt to secure the lock in place, and Jane found herself staring between her legs in search of an upskirt. Jesus fucking Christ, she thought to herself, this bitch has got me thinking like Herman!

Dickie couldn't leave the house naked. "Didn't you say you had some frilly panties?" Jane went to fetch them. Dickie's training had begun.

****

Herman stared at his computer monitor, stumped. He was going to do a 'who'd you rather', pink skirt versus turquoise, but Connie might not approve of it, which had to be taken into consideration. He surfed the Internet in search of inspiration, when he suddenly recalled the photographs he had taken. Connie posing with Dan offered nothing, as did Connie with Jovi, though seeing her hand on his ass got him erect. But Connie with Clem; that sweet, adorable, brazen young man had a lot of courage, placing his hand on her rear. But that wasn't as grievous a sin as sneaking up to her from behind and ejaculating on her, which is what he had done, so Clem got a pass. But it wasn't all bad. He had to blow up the image and use his mightiest software to sharpen the focus, but there it was; a hint of light blue panty, peering out from the pink behind. Herman had his own 'boing' moment, and he quickly forgot about writing a blurb on the blog. He grunted, panted, and pulled, and when he neared ejaculation he stood up and emptied his sack on the monitor, right onto Connie's pink skirt, which was enhanced by light-blue trim in a location where it mattered the most. Sometime in the future, long after the sperm dried and caked on his computer, once it impeded his ability to perv, he'd clean the mess but, until then, it would remain on his monitor and serve as a reminder of his devotion to the girl with the thick thighs and the short skirts.