The drive had been uneventful. Less than two hours on the Interstate from Kansas to Kansas City, Missouri and then the short drive north to the airport. He was staying at the Embassy Suites just south of the airport and she had the exit number. He was expecting her at 6:30 and she didn’t want to be late. He told her to drive carefully but she didn’t want to be tardy. First impressions are important and she knew she had to be respectful. From his messages he seemed very knowledgeable, someone who knew what he was doing, but Maggie was still apprehensive.
At work she was always in charge. Here, she knew, it would be different. She wasn’t afraid, but she was apprehensive. It always starts that way, with someone new, with apprehension. They were going to do role playing, something he called “The Story.” She knew it was intended to frighten her, to raise her level of anxiety. It was a subtle form of manipulation, and it was working. But she knew it was all part of the turn-on, something she craved almost as much as the pain and humiliation she would soon undergo.
He had phoned earlier in the day, before she left her home in Kansas, to give his hotel room number. Now she was at the hotel, using the house phone, telling him she had arrived. They had agreed on 6:30 and it was just 6:25.
He told her “If I’m not there, leave a message, I have to spank another woman at 4:00 PM, but it will take less than two hours. She’s your age, but she likes to dress up as a little girl, and I do her every time I’m in town. But I’ll have plenty of time to get back from down town before you arrive.”
She phoned and he was in his room. “I’ll be right down, meet you in the atrium. I’ll be wearing jeans and a black knit shirt. Might as well be comfortable.”
He asked what she was wearing and she told him. A blouse and slacks, easy to take off item by item. He came down in the elevator, spotted her right away.
“Hi, I’m Denis. You must be Maggie.”
He had a firm hand shake and a nice smile. That was reassuring.
He took her into the restaurant to talk. They ordered coffee. He told her he didn’t want her to drink alcohol before, didn’t want anything to deaden her senses. He told her he wanted her to feel and appreciate everything that was happening.
He told her something of his background. He had a technical undergraduate degree, an Ivy League master’s, 20 years managing corporate staff, the last ten developing computer simulation models and doing labor policy analysis. He didn’t mention if he was married, and he wasn’t wearing a wedding ring, but she guessed he was.
Maggie was in her early 40s, maybe 5’5″, 135 pounds. She needed to shed 10 pounds, and if this session went well, she guessed he could help with that “motivation.” She briefly described her work as a mid-level manager at a food processing facility stuck out in the middle of nowhere. She was very bossy at work and took a lot of it home with her. People who knew her might call her a first class bitch, but only behind her back.
Now that she had a new boyfriend, she needed to work on that, her bitchyness, of needing to get her own way all the time. She hoped a good spanking would help to re-adjust her attitude. The disciplinarian told her that when he was finished her butt would hurt for a few days, but he was sure she would be easier to get along with. After all, that was why she had just driven 140 miles.
He told her that she could use her own safe word if she had one, or she could use the two word combination, “Yellow and Red.”
This was all so new to her. She hadn’t been spanked since she was a child. “Yellow and Red,” she asked.
“Sure, it’s easy. Yellow at the point when you almost want me to stop, but know you can take just a little bit more. I’ll slow down then, give you a chance to catch your breath. And Red when you’ve reached your absolute limit and want me to stop immediately.”
He told her that he would spank her bare bottom, but he would let her keep her bra on. The idea of taking off everything except her bra added a new dimension, and Maggie guessed she would feel even more naked with her tits covered and her pussy exposed.
They had exchanged e-mail for almost a month before they met, and agreed to pick up “The Story” in real life where it left off. It went something like this: Her new boyfriend had hired a professional disciplinarian because Maggie needed some discipline. It wasn’t that he was a wuss, but he had never spanked a woman before, and wasn’t sure he could do it with any sense of authority. And the truth was that Maggie was really bossy at home and was always flirting with men at parties. So the disciplinarian would take her down a peg or two, humiliate her, make her beg, make her suffer.
The disciplinarian was going to spank her on her bare bottom, not once, but several times. She would be treated like a child, told exactly what to do, where to sit, where to stand, when to bend over. By the time he finished, her butt would be bright red, would sting as much as she hoped, would sting more than she hoped, and she would be totally humiliated.
She had just driven two hours to meet him, and this stranger had just told her all the things she wanted to hear, hoped to hear.
“Are your ready?”
In a little girl voice, almost a whisper, “Yes.”
“Good, then let’s get started.”
They took the elevator up to his rooms. In the living room he told her to unpack the things they would need, the things she had agreed to bring: the thermometer, the lubricant, her enema equipment. The enema equipment was her idea. She had given herself enemas regularly since she was in collge, but neither her ex-husband, or any of the other men in her life, had shown the slightest interest in putting a penis or an enema tube up her shapely ass. So the enema, the humiliation of giving up control of her body, was something she had dreamed about, something she wanted a man to do to her for as long as she could remember.
When they were ready, when he told her to, she would mix the enema solution, nice and warm and soapy. “There’s no sense mixing it now and letting it cool down,” he told her, and she knew that was true. And besides, standing there with her bare butt showing, bent over the sink, would be fun to watch. It would be another nice humiliating touch.
In “The Story,” she was recovering from the flu, so he would need to take her temperature before the spanking.
“No, I’ve changed mymind, I wouldn’t let you.” She wasn’t going to let him put a thermometer up her ass. “And besides, I’m not a child, you can’t take my temperature that way.”
“That was the agreement.” The was anger in his voice.
“No, you can’t, you’ve no right.”
“All the right in the world!” He sounded tougher than when they talked over coffee.
Then, out came the ruler. He told her before that he liked to use the ruler, had mentioned it an early chapter of “The Story.” The ruler was solid oak, 18 inches long. He told her it would hurt, but not as much as an English school cane. Maybe next time, if she didn’t improve, he would have to use the cane on he sexy ass.
So he did what she knew he would do. He turned her around, give her two or three across her butt with the ruler standing up, and then made her lean over the table in his living room.
“No, I’m not a child, you can’t treat me like one.”
Half a dozen on the seat of her pants. Not that hard, yet. Then he gave her six more, still through her slacks, still not too bad. After that he made her lower her slacks, down to her ankles. Then six more, evenly spaced from the fullest part of her ass to the middle of her thighs. They were beginning to sting.
“Ready for the thermometer?”
“Half a dozen more. If you’re still not ready, you get the slipper.”
Thwak! Thwak! “Count please, no credit if you don’t count.” Thwak! Thwak!
“One, two, three, four, five, six.”
“Defiance gets you EXTRA.”
So he gave her three more with the ruler, slightly overlapping, right on the fullest part of her very sexy ass, before he went to work with the slipper.
As he told her over the Internet, the Tai Chi slipper didn’t look like much. He showed it to her as she leaned over the table, her head resting on her arms. The slipper had a black cloth top and an orange rubber sole with dimples in it, European size 40, made at the Red Dove Factory Number 1. And as he promised, it did have plenty of sting. Rather than hitting down on her backside, he hit up, with a slapping motion, catching the underside of her ass, just at the tops of her thighs. Maggie was not a small girl, so there was plenty of back side to work on.
He gave her 12, six on each side, alternating left and right.
“No, Sir. A young lady ALWAYS address her elders as Sir.”
After that he lowered her panties to mid-thigh and began to work up the backs of her legs, up to the swell of her ass, and thendown again.
Thwak! Thwak! Thwak! Over and over …
“What about the thermometer?”
“Can I have it?”
Thwak! Thwak! Thwak!
“The thermometer, Sir.”
“The thermometer is there on the table.”
“In my ass, Sir. Please, can I have the thermometer in my ass?” Maggie was beginning to sense her own defeat, beginning to sense she had finally found a man who could control her.
He stopped for a moment, took the thermometer from its case, and shook it down. Next he got the thin rubber glove, put it on, and slapped her on the ass with his gloved hand.
“Spread your ass, nice and wide,” he ordered.
“Please, don’t make me do that.” How did he know exactly how to humiliate her?
He gave her a bare hand spanking on her tender bottom, eight or ten swats, very hard, and that was all it took. Maggie reached back with both hands to spread herself. Then she felt the first cold dab of KY, the familiar cold as he touched the pucker of her asshole. With a slow circular motion as he invaded her rectum with the tip of his finger. Then more KY, more cold, as his finger went in slightly deeper.
Here she was, a grown woman, bending over a table, her bottom totally bare. Then the discipliniarian began the slow in and out motion with his finger – loading her bottom with lube.
“We don’t want the thermometer to go in dry.” was all he said. That was when Maggie began to feel the crushing weight of humiliation.
Then he started with the thermometer. At first, he put in just the tip, the cold metal tip. Then he slowly pushed it into her rectum, so that only an inch was sticking out.
“Don’t move. Five minutes. Then well take it out and see if you’re well enough to be spanked.” Of course she would be well enough, but it was all part of their little game.
And he stood there and watched. She was glad she still had on her slacks, down around her ankles, and her panties at mid-thigh. It would be more embarrassing when she would be bare from the waist down.
“Two more minutes.”
Time seemed to go on forever. Finally, he took out the thermometer. He took it out slowly, withdrawing only a fraction of an inch at a time, twirling it a little, making her wait. He really knew how to torment her. Then the verdict.
“98.6, perfect, couldn’t be better for a spanking. Now stand up, and pull up your panties, so you can take off with your shoes and step out of the slacks.”
He instructed her to fold her slacks neatly and place them on a chair, along with her blouse.
“You can keep on your bra, for now. Wipe off the thermometer and return it to its case, and then go into the next room and kneel on the bed.”
She hesitated and hit her again with the ruler.
“Kneel on the end of the bed, facing the headboard.”
“Please, what?” and he hit her again. “Now march.”
Maggie quickly undressed. He nipples were hard and very visable through the sheer cups of her underwired 36-C bra. Part of it was fear, but part of it was sexual arousal. She wasn’t sure what would happen next, but she did as she was told. On the pillow at the head of the bed was a small vibrator, a Pocket Rocket, the one he described in his last posting, the one she had seen the novelty store at the Mall. It was made of hard plastic, only about five inches long, not too wide, an off white color. Next to it was an unopened condom.
He brought the tube of KY with him, and the slipper. First he handed her the condom and told her to open the package, and then to pick up the vibrator.
“Now roll the condom onto it.”
She paused and he smacked her sexy ass with the slipper.
Then he got back into “The Story,” the fantasy they were going to act out.
“You don’t understand. You’ve been a wise ass lately, so your boyfriend devised a cure.”
That was part of the reality. In real life Maggie was divorced. She had married late, and it didn’t take long for her ex- to decide she was just too big of a pain in the ass, too pushy, to difficult to deal with. The marriage had only lasted eight months. After several failed relationships, she was was dating a new guy, someone with long term potential, which was not an easy feat if you live in the middle of Kansas. Maggie really liked him, and she hoped the disciplinarian would give her a way of making the relationship work.
Then he smacked her again, an upward shot to the crease where her butt met the tops of her thighs. She would do what she was told. He took the vibrator from her.
“Now lower your panties, just a little bit, just below you bottom.” She was quicker this time and didn’t get hit. Then he made her lean forward, rest on her elbows, her head down. She wasn’t quite quick enough this time, so he used the slipper on her sore bottom, gave her six or seven, really hard. Now she could feel the burn.
He stood in back of her, told her he would start with his finger, then the vibrator. The vibrator wasn’t very long or very wide. Over the Internet Maggie had confessed she was still an anal virgin, but he assured her she would have no trouble taking it in her ass.
“No, you can’t.”
Five or six hard ones. Thwak! Thwak! Tthwak! Thwak! Thwak! The pain was very intense.
“Yes, please, Sir, can I have it?” from Maggie.
“Please, can you have what?”
“Please, Sir, can I have the vibrator?”
“And where do you want it?”
“Please, Sir, in my ass, Sir.” Her voice was barely a whisper.
“Then reach back and spread for me again.”
This time Maggie did as she was told. Again she felt the familiar sensation of the lubricant, the familiar cold of KY straight from the tube. Then his finger was going into where the thermometer had been, slowly into her rectum. He went in slowly, always slowly, all the way up to the knuckle. That was very nice, she thought to herself, followed by, and you’re turning into a real slut.
“I think the vibrator will fit.” And what about a penis, Maggie thought to herself.
Then he stood in front of her, made her watch as he slowly lubricated the vibrator with the condom on it.
“This was your boyfriend’s idea. He thought it would smarten up a smart ass.”
Then he stood in back of her, put the vibrator against the pucker of her asshole. Till that time, she had never been so humiliated in her life.
“Relax and exhale.” She did as she was told and he slowly pushed it into her. “Don’t let it come out. If it does, I’ll make you do something very unpleasant with it before I let you put it back, something that will leave a very unpleasant taste in your mouth.” G-d, she hoped he wouldn’t add to her humiliation by making her lick her shit off the vibrator.
Then he turned it on. She could hear it, feel the hum, feel the vibrating deep inside of her. “Five minutes.” She quickly reached back to hold it in place, careful not to turn it off, as a tear began to form at the corner of her eye and run down her cheek.
It was a long five minutes, kneeling on the end of the bed, her butt up in the air, her head down. Maggie had to use one hand to hold the vibrator in place, which made it more awkward. He had warned her, if it came out, he would make her do something very unpleasant with it, before he let her put it back, and then they would have to start all over.
It didn’t hurt, having the vibrator inside of her. She could feel the humming, feel the strange sensations it was sending through her rectum. It was different from the enemas she had given herself, a different kind of fullness. She thought maybe if she was alone, not kneeling on the end of the bed in this humiliating position, she might even like it, a vibrator in her ass when she was home alone some night, masturbating before falling asleep.
She wished he would have pulled up her panties, held the vibrator in place that way, but she wasn’t that lucky. Maybe if she asked.
“Please, Sir, can you pull up my panties?”
“What for? ” “To hold the vibrator, Sir.”
“Fine with me.”
He pulled up her panties. That pushed the vibrator another inch deeper into her rectum, but now she was sure it wouldn’t come out.
“Now five more minutes.”
And he hit her on the backs of her legs, high up, several times, with the slipper. She could feel the vibrations all the way to her rectum.
Finally he said “Time is up. Now let’s talk.” He didn’t say he would take out the vibrator, or that she could take it out, and she dared not risk it.
“Your boyfriend tells me you’re a real flirt.”
Using his finger tip, he tapped very very lightly on the end of the vibrator and it sent the vibrations deep into her rectum.
“Oh, my.” It didn’t hurt, it was just different.
“Once again. Your boyfriend tells me you’re a real flirt.”
Another light tap on the vibrator. This time “Ahh.” Maggie was confused.
“That at parties you like to wiggle your ass, like to brush it up against other men.”
Another tap on the vibrator. Another more insistent “Oh! My!”
“He thinks you act like a tramp. He wants you to clean up your act.”
Then the slipper on her butt, that upward shot again.
“The correct response is ‘How, Sir?'”
“Yes, please … How, Sir?”
“With a nice, warm, soapy cleansing enema.”
Maggie’s heart sank. She knew it would come to that. She had traveled over 100 miles, had been spanked and humiliated, and now the final defeat. But wasn’t that what she wanted?
“I can beat you all night, with the slipper or the ruler, until you’re ready, or we can get it over with.”
“Please don’t beat me.”
“Sir!” he shouted.
“Please don’t beat me, Sir.”
“And what do you want instead of another beating?”
Maggie knew the answer, but didn’t want to say it.
“Do I need to get the ruler?”
“No, Sir. No more ruler. An enema, Sir.”
“Why do you want an enema?”
“Because, because, because I need to clean up my act, Sir.”
“And what act do you need to clean up, Margaret?’
“I’ve been a flirt, Sir, but I won’t be any more.”
Two more taps on the vibrator. “Oh! Oh!”
“Please, Sir, no more. I promise I won’t flirt. Please can have my enema?”
Finally, the first part of her humiliation was over.
Maggie knew she had been willful and disobedient, hard to get along with at work, an uncontrollable flirt. Her new boyfreind had been right to hire the disciplinarian.
Maggie was broken in spirits. Here she was, a grown woman, a company executive, over 100 miles from home, kneeling on a bed in the hotel room of an almost complete stranger, a vibrator lodged firmly in her rectum, begging him to give her an enema. She knew the second part would be worse.
What were the words she had just said:
“Please, Sir? Can I have my enema?”
And so the second humiliation began.
He lowered her panties and removed the vibrator. It wasn’t clean so he put it on a tissue on the desk. Then he told her to stand up and take her panties all the way down, to take them off completely. He didn’t want her to get it dirty if she lost control. She moved as if in a trance.