“Jake, I have heard from Josephine. It’s a mixture of good news and somewhat ambiguous news,” Livia said.

“Then give me the good news first,” he replied.

Jake was Livia’s boss at the offices of a small restaurant chain. At twenty-six, he had already become the head bookkeeper. Livia, at the age of twenty, was his assistant. He had recently caught her embezzling a small amount of funds. Rather than report her or press charges against her, he met some of his own less than savory needs by taking her across his lap and whipping her bare behind with his belt.

Since her punishment, Livia had been dressing up more for work. It seemed best to finally look like an adult, not an overgrown teenager. On this day she wore a blazer and tight gray trousers. She knew Jake had been checking out her compact ass in her new pants. Let him look; he’ll have plenty of real things to worry about when Josephine grabs him. Meanwhile, her new look gave her a sense of power as she went about her office duties.

Josephine was Livia’s friend, and she had a pronounced kinky side. She was a switch, and she liked to both dominate and be submissive to men at different times.

“The good news is that Josephine has agreed to meet you. The sort of ambiguous news is that she’s going to be in dominatrix mode on the first meeting.”

“I thought I was going to have a date with her first.”

“That is the first date. If that goes well, you will meet again for a so-called regular date. You know, dinner, a movie, that kind of thing.”

“So when do we get to the sex?”

Livia laughed at him, “I can see where your mind is at. One thing at a time. You need to know more about how this first one will go.”

“I was wondering about that. How does she define, ‘going well?’ ”

“I do know this; give me a moment to describe things. On this first date, she is going to start in the dominant mode. She’s an amateur, not a professional, so she’s not going to discuss it in great detail first. You will indeed have a safe word, which she will text to you beforehand. You do know what a safe word is, correct?”

“Oh yeah, I’ve heard of that.”

“Well, my recommendation is that you not use it on that first day, if ever. I think she’s going to use her hairbrush and a leather strap on you, but take it like a man. Yell and bounce around if you wish, but don’t call it off. You’ll make a big impression on her if you can endure it; in fact, she will respect your courage. Ah, have you ever been spanked by anyone, even your parents?”

“No, never.”

“Then you’re in for a novel experience. By the way, the pretext for all this is that she is upset that you punished her friend, namely me.”

“But I had to do that; you had stolen from the company.”

“I said it was a pretext, not a reality. Now, when you’re over there, remember to call her Miss JoJo, got that?”

“Really? Why is that?”

“That’s her dom name, you might say.”

“Livy, do you have a photo of her?”

“Right, I almost forgot. I’ve got some here on my phone.” He looked at the pictures which showed a dark-haired woman with a slightly round face. Livia continued, “She’s not skinny; she’s got a bit of curvy chunk on her. That doesn’t bother you, does it?”

“Not at all. Is she Italian, perhaps?”

“Good guess; she’s half Italian and half Greek, a product of the Mediterranean. But she’s good, right? Not too cute and dainty, but a real nice solid lady. Big, beautiful tits, too.”

“You said she’s actually a nice person too.”

“Absolutely. Now, you will have to do other bits of submissive business in this first session, but nothing too extreme. Like, if she asks you, no, tells you, to get a drink or something else for her, then get it. She might also ask you to kiss her shoes or something.”

“That sounds disgusting.”

“They’ll be new ones never worn on the street; practically fresh from the box. Anyway, this whole thing will be, well not all day, maybe a couple of hours at the most. Then a day or two later, you will call her and ask for a real date. No, don’t ask, just tell her you want to go out with her. She’ll go, believe me. Sounds good so far?”

“I don’t know, this is all kind of new to me.”

Livia almost asked him, do you mean going on a date at all? However, she held her tongue.

She continued, “Now the third date, that will be interesting. She’s going to be submissive for that, yet she will let you know, subtly, how it should go. I’m sure you will be able to give her a good, sound whacking on her ass. Chide her for being a bad girl, or whatever. She’ll let you know exactly what’s bothering her.” Livia thought for a  moment. “And then the best part of this: she’s going to sexually submit to you as the finale.”

“Are you sure of that?”

“As sure as I am of anything. Just don’t fuck up that first date, the one where she dominates you. Just follow what she tells you to do, and it will be fine.”

Livia thought to herself, am I really doing this for Josephine, or is it for myself? Could it just be a little bit for him?

No, it couldn’t be for that, not with the cruel way he punished me. I’d like a counterstrike of my own, but that’s just a fantasy. JoJo will have to do it for me. Of course, JoJo is also going to alternate and get spanked herself, as well as fucking Jake’s brains out when she’s in submissive mode. It was a halfway compromise, but it the best she could come up with.

Jake asked Livia one more question, “What happens if I get, you know, turned on by all this, I mean in the first session?”

“She knows that could happen.” Livia smiled, “If you get a boner, well, then you will have a boner. Don’t get embarrassed or try to hide it.”

******

Jake had an experience with a woman once before, a very serious affair in fact. When he was in college, he even got engaged to her. His beloved was named Alicia; she had been the love of his life so far.

But something had gone wrong. Perhaps he had worn his heart bit too much on his sleeve, and she lost respect for him. But whatever it was, she dumped him for an older guy who ran his own financial consulting business. A mere bookkeeper couldn’t compete. That had ended just after his last senior semester at college, four years earlier. He didn’t make a good transition to adult dating. Perhaps he would have done better in the 1990s or earlier, but when he hit the scene online apps dominated the dating world.

He thought he just wanted a “nice” girl, but he couldn’t find one in the digital maze. He didn’t have the looks or money to really get a lot of attention. Tinder was the absolute worst; there seemed to be no room for the likes of him at all on there. It appeared that women held all of the cards in this online environment. He swiped right on a number of them, but only a handful would return a message. None of them agreed to as much as a coffee date with him.

He did feel a bit guilty about what he had done to Livia.  I did it basically to see her ass, and since I couldn’t fuck her, I beat her instead. That was her opinion too, and she had been right.

Yes, he had caught her stealing, but if he had really wanted to give her a break, he could have just asked her to pay the money back, in installments if necessary. But for a few months, he had been looking for a good excuse to spank her, and the embezzlement was the perfect opportunity.

He knew little about JoJo besides the fact that she had been married for two years; that had ended at least a year earlier.

*****

On the evening of the first date, Jake wore a sports coat and a tie for the drive over to Josephine’s little house. He knew a few ground rules that Livia had told him.

One was that he should always call her Miss JoJo when she was in the dominant mode. Another was that, when he was being submissive to her, he should be polite but not grovel unnecessarily. She was going to beat his behind with her hairbrush and probably a leather strap or paddle. Livia had said, “If I could take it as well as I did, I think you will too.”

He knew that his safe word, or phrase, was “chicken salad.” That was the one Livia herself had made up during her own fantasy after her punishment.

When Josephine opened the door, she didn’t look that menacing, but neither did she smile at him. Like Livia had predicted, she was wearing a business suit – a black one. The skirt looked like it was a size too small for her. In any case, it was quite tight on her body. Her black shoes had high heels and her nylon stockings were dark too.

Jake thought she looked even better in person. Her dark hair was pinned up on her head. Her body had a pleasing roundness; she was definitely not a willowy chick. She had seen photos of him too, so she already knew what he looked like. He figured he’d get in the first word, “Oh, hello, Miss JoJo. Pleased to meet you.”

“So you must be Jake. Come in; I’ve got to something I want to talk to you about.”

As soon as they were in her parlor, she sat down on the sofa but she said to him, “Don’t sit down unless I tell you to. This is my home, and I have a serious issue to talk about. First, get me a drink. I want a Manhattan.”|

“Ah, I don’t know how to make one of those.”

He was surprised that she was matter-of-fact about it, not overly rude. “Go into the kitchen and get a martini glass. It’s made out of rye whiskey, with some sweet red vermouth and a dash of Angostura bitters. You stir it all over some ice, then strain it into a glass. Serve it straight, no ice, but add a Maraschino cherry as a garnish.”

He hesitated for a moment and she said, “You’ll find everything you need in the kitchen. Don’t obsess over the portions, but the rye should be the main ingredient.”

Jake was surprised at how nervous he was while making her drink. I hope she likes it. But when he brought it in, she said nothing. He just stood there as she spent a few moments savoring her Manhattan. I feel like a waiter, but I guess that was the point of all this.

After a bit, she put down her glass and said, “Now, I know what you did to my friend, and it’s completely unacceptable.”

Jake thought he could defend himself, “But I did catch her stealing.”

“I know that, and you did give her a break by not charging her or reporting her. However, you could have simply had her pay back the money in installments, maybe even with interest. But no, you had to use that as a pretext to indulge your proclivities.”

“But, I am the boss there.” That sounds kind of weak.

Josephine replied, “And I’m the boss here. Now, I heard how cruel you were to her. You spanked her with your belt and you didn’t stop until she cried. Tell me, Jake, in your role as boss – have you ever spanked girls before?”

He told her something that even Livia didn’t know about. “Well, yes, Livia’s predecessor, a girl named Cynthia, she was tardy a lot. I spanked her by hand a couple of times.”

“And why did you feel the need to use your belt on Livia?”

Jake felt compelled to be truthful. “You see, when I did that to Cynthia, my own hand got sore too. It was numb, in fact, when I was finished.”

Josephine pondered that. “So, you’re quite clever. You decided to maximize Livia’s pain to avoid any of your own.”

“I guess that is true.” Why am I admitting all of this to her?

JoJo waved her hand, “It’s already done. You have abused your authority as a boss. I know you also enjoyed looking at Livia’s bare behind for its own sake. But your excuses don’t cut it with me. I know what they are, merely pretexts to justify it to yourself. Thus it’s now your turn to pay the price.”

She took more sips from her Manhattan. “So Jake, first I’m going to take you over my knee and spank your ass with my hairbrush.” He hadn’t noticed it before, but she had the thing on the side table. As Livia had said, it looked impressive. Jake suspected it had been made for discipline purposes; it looked far too big for merely brushing hair.

“All right, take your trousers down, your underpants too, and get over my lap.”

Once there, he was surprised at how exciting it was to have JoJo staring at his bare behind. It’s been a long time since any woman has seen his body in that way. He also liked the feeling of his bare crotch pushing down on the cloth of her skirt.

He was surprised by what she did next. She rubbed his behind and the backs of his thighs; she also squeezed his butt cheeks. He was instantly erect, and he knew that she could feel it.

“You are quite a bad boy. You are as stiff as a pole.”

“I can’t help it, Miss JoJo.”

She continued the delightful rubbing. “I know that. You are a bit thin, but you do have a nice taut ass. It’s too bad I have to punish you on it so severely.” Jake held out hope that she did find him attractive, and he would benefit from that although definitely not on this day.

The last thing she said was, “If you want some chicken salad, just let me know.” Of course, that was the safe phrase.

He put on a brave front, “I’ve never liked eating that stuff.” That was actually true. When he was a boy, he had gotten sick from eating a bad batch and he had thrown-up. Since then, he couldn’t abide consuming the stuff.

She gently rubbed the back of the brush across his rear end, which felt pretty good in itself. She used her left hand to hold me around the waist, and she held the brush above him with her right. Then, without warning, she began whacking him with it. He yelped with each blow; he couldn’t control his voice.

He had never been spanked before, not even by hand, not even over his clothes. Each blow by the hairbrush seemed to drive air out of his lungs, and that emerged as a kind of groaning yell.

JoJo said, “Not only have you been a very bad boy, you have also been an irresponsible boss. You’ve spanked girls because your authority allowed you to get away with it.”

Jake was somewhat surprised by the intensity of the paddling, and yet his cock remained erect. JoJo noticed that too, “My, you’re still stiff. That’s not too surprising; the buttocks are an erogenous zone. However, I bet that I can get that stiffy to go down if I try hard enough.”

She took turns whacking each side of his butt, one after the other. The backs of his thighs also go some attention at random points. He wriggled around, and then he strained his body forward. His feet scraped against the floor. He remembered Livia’s feet doing the same thing when he had used his belt on her.

Surprisingly, JoJo praised him for his fortitude. “You’re taking this pretty well, considering how bruised you’re getting. And believe me, you are getting bruised quite well.” She stopped for a moment and poked him with the brush. It was a tender spot, and he gasped as the wood pushed down it.

She said, “That wasn’t surprising. That spot has been hit several times already, and it’s redder than the rest of you.”

It went on for a while, and Jake tried to show some grit by not making too big a fuss about it. Nevertheless, he couldn’t control his voice, and each stroke caused him to yell or groan. Yet he found it bearable, even oddly pleasurably. He liked the intimacy of being pressed against her body, and the feel of her hand holding him around his waist.

Finally, she stopped and put the brush down. Then she took to rubbing his hindquarters again, except this time they were extremely sore and tender.

“You really feel hot back there. That’s to be expected. Does this rubbing make you feel a little better?”

It did, to some degree. “Yes, Miss JoJo, it feels . . .” He wasn’t sure how to finish the thought.

“That’s okay, your cock was erect the entire time. You seem to be a natural-born sub.” It’s funny how Livia had already predicted that.

“Okay, you can get up and rub yourself now.” He was grabbing his own ass before he could even get up from her lap. When he was standing up, his cock was still jutting out, very stiff and erect.

JoJo commented on it. “I’m really not too surprised. I find that many people with sadistic tendencies have some masochistic feelings too, and vice versa.” Jake thought but did not say, yes, and you are a perfect example of that.

After a few further moments of comforting his own backside, he heard JoJo say, “Now it’s time for phase two, the leather strap. It’s kind of a bit of extra seasoning on top of the main course.”

She had the strap on the floor next to the coach. It was thicker than a normal belt, and Jake speculated that it too had been specifically made as an instrument of corporal punishment. Where does she get these things? Later, he would look online and find that is easy to order just about any discipline implement imaginable. He had thought, eventually, even Amazon will be offering this stuff for sale.

Josephine said, “Now for this, you are going to bend over the armchair over there and put your hands on the cushion. Let’s see, the English use the phrases, ‘six of the best’ or ‘twelve of the best.’ I think eighteen strokes would appropriate for you.”

She must have noticed his expression, because she continued, “Don’t feel too bad. In Scotland, male students routinely got thirty-six blows of the tawse, which was actually longer and thicker than the strap I am going to use.”

When he got the first stroke of the belt, he uncontrollably stood upright. JoJo was fairly mild about it, “If you feel the need to get up, hold on the arms of the chair and brace yourself. But stay in position.”

The strap felt different from the brush. While the latter had made hard impacts on specific spots, the belt swiped his ass from one side to another. About halfway through, JoJo stopped and said, “It’s interesting how the marks of one implement mix with the marks of another.”

Jake thought he could stand it, however. When she reached the eighteen mark, JoJo said, “I think you could use a few more, just to seal the deal.” She gave him seven more, for a total of twenty-five.

He remained there, breathing heavily and still gripping the arms of the chair. He heard her say, “Okay, you may comfort your ass again. Then, stand facing the wall with your hands on your head. I want to admire my handiwork.”

Once he was standing there, Jake could feel his behind radiating heat. It also seemed to be vibrating, although that perhaps was an illusion. JoJo, meanwhile, went back to the sofa and was finishing her Manhattan. She said, “I see I did a thorough job on you, but I always do. I suspect it’s going to be a long time, if ever, before you think of spanking your female employees again.”

She had another comment, “Jesus, you still have an erection. Livia was right, you are a sick little puppy.” He caught a tone of good-natured teasing in her voice.

She didn’t prolong this phase. After a couple of minutes, she said, “Okay, corner time is over. Get your pants up and get me another one of these.” She held out her now empty cocktail glass. “Make it another Manhattan.” Jake felt like he could use a drink himself by now, but he knew enough not to ask for one. I can have something when I get home.

When he returned with her drink, she said, “Before you go, I have one more bit of humiliation for you, I’d call it. Get down in front of me and kiss my shoes. Lick them, in fact.”

He looked down, and as Livia had promised, they did look shiny and new. Oh well, how bad could it be?

While he was down there, she sat with her legs rather far apart. He looked up, and he could see all the way up her thighs. She was wearing a white garter and straps to hold up her stockings. On top of those, she had dark underpants that were pretty much transparent. Her cunt slit and her pubic hair were clearly visible through them.

Jake knew enough not to comment, but he dared look up at her face. She had a slight smile. Her message seemed to be, yeah, I’ve got some pretty cool stuff on under there. What she said was, “Since you’re down there, don’t miss the heels too.” He dutifully kissed and licked those parts of her shoes too.

When he was allowed to stand up, he saw JoJo playing with her hairbrush, moving it back and forth in her hands. “All right, Jake, I think you’ve learned your lesson. You’re not going to be spanking Livia or any other female employees again, I assume?”

“No, Miss JoJo, I’ll never do that again.”

“That’s good. Because, if Livia tells me otherwise, I’m going to have you back here for something even worse.”

Jake could grasp the role-playing aspects of all this. He was well-aware that Josephine had no real authority over him and she couldn’t compel him to do anything. Nevertheless, he had been promised some good things for his own benefit, although that couldn’t be discussed today.

Then she waved her brush at him, “You are dismissed. I assume you are capable of letting yourself out.”

He thought he should be polite before he left, “Have a good day, Miss JoJo. It was nice meeting you.” He feared he had said something ridiculous, but she gave him the merest smile and she nodded.

Once outside, he looked at his watch and noted what a brief session it had been. Just long enough to get the job done. He had to gingerly lower himself into his car seat. At home, he looked at himself in a mirror. JoJo had indeed done an impressive job in disciplining him. His entire backside and his upper thighs were a mixture of red and purple.

When he went to bed that night, of course, he masturbated thinking of Josephine. She had taken her skirt and panties off, but her open-bottomed garter allowed access to her crotch. He imagined her straddling him cowgirl style on her sofa. It was a very intense fantasy, and when he came, he was impressed by how far out his own spurts went.

Afterwards, he lay there and considered his situation. He wondered if this new relationship with Josephine – if indeed it was a relationship – was going to work. He hadn’t even met the real her yet; she had been playing a role. Yet it seemed that he had done everything he could to follow his own part correctly in the scene.

In the last four years, he hadn’t even been on a single date with a woman. He had almost forgotten what it was like, and at times he had given up hope of ever finding someone suitable for himself. He knew he shouldn’t obsess about it now. Within a day or two, he would find out what the next steps, if any, would be.

#####