Jenny was running late. Seems like she was always running late, sometimes it was her fault for not planning ahead, sometimes it was unforeseen circumstances.
But it didn’t matter to him. To him, it was always her fault–either directly or indirectly. She should have left earlier or she should have anticipated there would be a problem and made allowances for it.
Today the traffic was heavier than usual… and then there was the road construction and the detour that took her blocks out of her way and through busy intersections to boot.
Dammit, she thought as she sat waiting for the light to change, I’m going to be in so much trouble when I get there!
As she sat there at the intersection, she shifted in her seat. The leather seats in her car, a Mercedes C Class coupe, were making her ass sweat and itch a bit.
He had given her explicit instructions she was not to wear panties to meet him and now, with the warmth of the Southern California sun and the excitement of what promises to be, sitting there at that intersection was becoming more and more distracting!
Bored and with her imagination on overdrive, she slid the hem of her already too short little black dress higher up her nylon-encased thighs.
She had picked out this dress knowing that it was tight to show off her curvaceous figure, short enough to be exciting and yet acceptable in public, and naughty with a plunging neckline that showed off plenty of cleavage from her large enhanced tits.
Jennifer McMillan was a former fashion model and had also done some work for popular men’s magazines, so she knew a thing or two about appearances and how to “dress to impress”.
She had made a very good living at her chosen profession, and now was living quite comfortably on her retirement savings, public appearances, and her investments.
She’d been smart to hire herself a very competent investment counselor who made some shrewd investments for her and they had paid off handsomely. Ms. McMillan did not lack for money!
What she did lack for was companionship–specifically male companionship. Curiously, because she was so famous and so beautiful, men often shied away from her, afraid to approach her thinking that either she wouldn’t want anything to do with them, or that she already had so many men they were dripping off her like the rain.
The reality of it was neither case was true. She was a beautiful, desirable, sexy woman, but also terribly lonely and sexually frustrated.
Which is how she came to meet the man she was on her way to see now. A couple of years ago, she was on a photoshoot for yet another big-name magazine, when she was told she needed to attend a very upscale party thrown by the publishing company and the magazine to promote it. They were trying to bring in new markets and new investors, and they wanted her to make an appearance since she was the cover model that month.
While she was at the party schmoozing the men and women with the purse strings, she saw a well-dressed man sitting at a small corner table by himself. She noticed he wasn’t paying a lot of attention to what was going on around him.
He seemed somehow to be disconnected and not bothered by the persistent drone of multiple conversations going on around him. Almost as if he was above all that noise. It puzzled her since everyone was there for the express purpose of getting their pockets picked by the magazine and publisher.
Jenny sauntered over and tried to make polite conversation with this nonconformist. “Hello, mind if I sit with you? I really hate these things–they call them parties, but all they are honestly are fundraisers for the magazine. And I seem to be the ‘bait’ tonight!” she said with a big smile.
“So it would seem. But if you are the ‘bait’ then I have to tell you that these people know how to fish!” he said, complimenting her. Jenny blushed and thanked him for his kind words.
From that point on, they talked and she spent the rest of the party not too far away from him. She had to go say hi to some of the other guests, but always kept her eye on him and returned as soon as she could.
As the night wore on, Jenny unknowingly fell for this lone man’s charms and appeal. She found him very easy to talk to, a wonderful listener, and not the least bit judgemental.
He let her talk about herself, her career, her goals, and other things which she loved, both as a model and a woman. He would interject every so often to show he was listening, but that’s mostly what he did–listen.
By the end of the party, Jenny was very interested in the man she had met. However, when the time came to go home, he gave her a polite goodbye, telling her he enjoyed their talk and he left without any further commitment. She didn’t even get his name!
Jenny went home and tried to forget about the party and the man, but his unusual comportment and behavior kept with her. He didn’t act like anyone else at the party or anyone else she had ever met for that matter.
A couple of days went by and Jenny was sitting at home when the phone rang. It was him! She felt herself go weak in the knees at the sound of his voice and she went from a cool adult professional model to giddy schoolgirl being asked to the prom!
He told her that he had enjoyed their conversation as well and asked if she would like to go out on a real date sometime. She accepted without even having to think about it!
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Since then they had seen each other many times. Sometimes he came to Los Angeles on business, sometimes for pleasure. And each time he did, he made a point to see her at least once or twice before heading off to his next destination.
He was quite secretive at the start about what he actually did for a living, but as they got to know each other and build up some trust, he let her in more and more.
One day, he confided in her and said that he was a semi-retired computer security expert specializing in anti-hacking and identity theft issues.
He had worked with the L.A.P.D. and the F.B.I. in past cases, and now works with other well-known companies to keep their customers and company computers safe.
He told her he makes a very comfortable six figures a year doing this, plus he gets to travel all over the country and the world when a company has a problem they need his help on.
Jenny had been duly impressed. “I can barely work the computer well enough to email and check my Facebook and Twitter accounts!” she’d said with a giggle.
He had been a perfect gentleman when they first started seeing each other, not even trying to get her to sleep with him until the third date.
“I want to know you from the inside–I already know what’s on the outside. I want to set up house in your mind and then I will explore your body… one has to have a base from which you can travel!” he had said.
Jenny smiled–he had certainly set up a “base” in her mind; he was all she had been thinking about since he called her a week ago and said he was coming to L.A.! She thought about the times they’d had together.
And the sex! Oh my God, the sex! His gentlemanly manners and patience in waiting to have sex nearly drove her out of her mind!
She was ready to go to bed with him on their first real date, but he made her wait… he made her wait while his words and actions made her melt!
When he finally did take her after he had teased and toyed with her that whole evening, it was the most incredible, unbelievable, earth-shattering thing she had ever experienced! He took her to places even her most erotic nighttime fantasies didn’t know about!
As she thought about their past sexual escapades, her hand subconsciously dropped to stroke up the inside of one thigh until it reached her crotch.
He had, in past conversations, told her he liked a shaved pussy and after demonstrating his penchant for cunnilingus and the talent with which he used to do it, she was more than happy to shave and keep it that way for him if it would encourage him to dine on her more!
She had made sure she was smooth as a baby’s bottom for him this evening and as her hand reached her smooth slit, she also felt the wetness that confirmed she was more than a little excited to see him again!
At last, the light changed and Jenny was able to continue on her way. A couple of minutes more and she was able to get back on the road she needed to reach his hotel.
She looked at the clock on her car dashboard. Shit! She was now twenty minutes late and she still had about five minutes, if she was lucky, before reaching the hotel room.
He was gonna be pissed! One thing she had learned from him is that punctuality was high on his list of desirable traits. And she had blown that one!
She glanced at her purse thinking she should call him and tell him she was running late. But by now, the fact that she wasn’t there with him would tell him that. Besides, it would be better to apologize to him face to face so she could explain what had happened.
Not that it would do any good, but at least he could see how sorry she was. He wasn’t one to accept excuses, even if they were valid.
As much as she wanted to hear his voice and see just how much trouble she would be in, she decided that she just needed to concentrate on getting there as fast as she could.
After an excruciatingly long seven minutes, she was pulling up to the hotel parking lot. She found a spot close to the front door and quickly parked. She ran as fast as her high heels would allow into the lobby and straight to the elevator.
He had told her what floor and what room he was in when he called her the other day. He had meetings and business to take care of before he could meet with her he had said, but the delay had only exacerbated her desire to see him.
Once on the elevator, she had a chance to catch her breath and gather herself a bit. She could feel the shivers of excitement running up and down her and her heart racing. She had to will herself to calm down just as she did before a magazine shoot or runway appearance.
The Renaissance, being a very nice five-star hotel, had full-length mirrors installed on the walls of the elevators for the guests to check their appearance before getting to the lobby and public view and that’s what she did.
She checked her hair, her makeup, and adjusted her dress a bit. She was already in trouble for being late–no sense in compounding it by showing up looking shabby!
She got to the hotel room he told her he would be in and she stopped at the door. Taking a deep breath, she knocked on the door softly.
Suddenly the door opened. “You’re late. I said be here at 6:00 and here it is 6:35. I was about to call the police thinking something might have happened to you!”
He pulled her into the room by her arm, letting the door close by itself and lock automatically. He led her over to the table where he had laid out all the toys and devices that he had brought with him.
“Do you see all this? I brought all these things with me to use on you and you couldn’t even see fit to get here on time to play.”
“I’m sorry! I left in plenty of time to get here, but the traffic was very bad and there was…” she started.
She looked at the assortment of dildos and vibrators and other “toys” and her pussy got even wetter. She felt a thrill and she knew that she was going to enjoy this visit!
“Quiet! You know how I feel about being on time. You live in this town, don’t you? You should know when traffic is bad and plan for it!” he said.
“Yes, Sir.”
She knew it was hopeless when she started explaining, but she’d hoped to at least get the explanation out. He didn’t want to hear her excuses, though. She was late and that was that. It didn’t matter why.
“So what are we going to do about your disrespectfulness?”
“Sir?”
He had never divulged his real name, preferring that she just call him Sir. It added an air of mystery that she found quite exciting, and it made her wet knowing she served a nameless man!
“Well, you were late. That makes me think my time isn’t worth a whole lot to you. That’s pretty disrespectful, don’t you think? What are we going to do to teach you to be more considerate next time?”
“Please, Sir, I didn’t mean to be late! Can’t we just forget it this time and start playing. I have been looking forward to seeing you since you called. I’m so wet and ready for you! Please?”
“I have been looking forward to seeing you as well. However, I cannot just ignore your tardiness. If I let you off this time, you might think you can sweet-talk your way on other matters, and pretty soon my authority would be undermined and useless.
“No, you need to learn that when I say something, I mean it. When I say be here at a certain time, even a minute past that is late. And just like when you were in school, tardiness has consequences.
“When you are late for a modeling job, do they just ignore it? When a fashion show starts at 5:00 pm and you show up at 5:30, do they just say ‘Oh well let’s get started now’?”
“No, Sir.”
“No, they do not. They either fire you and get someone else, or they punish you in other ways. Now, I’m not planning on ‘firing you’ and getting another girl, but I think some kind of punishment is warranted don’t you?”
“Yes, Sir.”
She could see he wasn’t going to let this go and she wasn’t sure she liked the way this conversation was headed.
“What…um… what are you going to do?”
“This is the first time I have been forced to punish you so it can’t be anything too terribly severe. But it has to be something that will make an impression on you. Now you are thirty-five years old, is that correct?”
“Yes, Sir. My birthday was two months ago.”
“I remember. Well, at thirty-five-years-old you are an adult, and because of your career as a top fashion model you are used to being somewhat catered to, am I right?”
“I guess so… what are you getting at, Sir?”
“What I am getting at is what would be the most humiliating, shameful thing that could happen to a spoiled rotten adult brat who thinks only of herself and disregards the feelings of others?”
“Sir?”
“A spanking my dear. I’m going to give you a good old-fashioned, over the knee, bare-ass spanking!”
“A SPANKING! B-but Sir, I haven’t had a spanking since I was just a little girl!!”
“I think we have hit on part of your problem! You have forgotten what having a red bottom does for a girl’s temperament!”
“But Sir, what about… I have a photoshoot next week!”
“Do not worry about that. I do not plan on leaving any marks that would detract from your photos. You will have a red ass when you leave here tonight and you might find it a bit uncomfortable to sit for a day or two, but it won’t leave any lasting marks on your body. I am not trying to train your body. I am trying to train your mind.”
“But Sir, isn’t there… some other way? Please, I promise I won’t be late again! This is so…”
“Jennifer, you were thirty-five minutes late tonight. We have been talking now for ten minutes. It will take probably another ten minutes to give you this spanking plus some time afterward before you are ready to do what we came here for in the first place.
“Do you really want to waste more of our precious time together discussing this? Or would you rather get the inevitable over with so we can move on?”
He seldom called her by her full first name so when he did this time she took note. “I’m sorry, Sir. Let’s get it over with. Please spank me so I will learn not to waste your time, Sir.”
“That’s better. Now take off that dress. Leave your stockings and heels on, though. I like that look on you.”
Jenny blushed at his compliment then stripped out of her dress quickly. She stood in front of him, naked now except for the heels and stockings he requested.
She trembled as he looked her over–he had that effect on her. But this time she wasn’t sure if it was her natural admiration and reverence for him that caused it, or this new aspect of getting a spanking that made her tremble.
He ran his hands over her body, examining her and caressing her. Jenny felt her knees get wobbly and her breath reduced to a soft pant as his touch set her flesh on fire.
God, this man could make her crazy! She may have walked into this hotel room a wealthy, thirty-five-year-old professional model, but one touch from him has reduced her to a shy, quiet, submissive young girl needing confirmation she is loved and wanted!
“Come.”
He took her wrist and gently guided her over his knees, laying her on the bed so that her ass lay directly over his knees and raised slightly for his hand.
“Now, as I said, since this is your first punishment spanking, I will go fairly easy on you. I want you to remember what we did here, but I will not be too hard on you. I still want to try to salvage some of this evening and have some fun. You did come here for some fun did you not?”
As he spoke soft and gently, his hand caressed her upturned ass, running up and down the backs of her legs and dipping between them and moving agonizingly close to her dripping pussy. She parted her thighs just a bit in hopes that he would touch her where she needed him to most, but he avoided that area, although the promise of his touch was never very far away.
“Yesss…”
Jenny raised her ass as he caressed her. She so wanted to have fun–she had been dreaming about nothing else for the past week and she was nearly on fire with desire for him.
His gentle caresses on her bare ass were not helping matters any, either. Even the idea of getting a spanking from him was exciting, and she wished he would get on with it. The anticipation was sheer torture for her!
He knew what his words were doing to her. It was obvious to him by the way she was leaking between her legs. It was obvious in the musky scent of a woman in heat she was giving off.
And it was obvious in the motions and sounds she was making that his words and his touch were pushing all the right buttons for her. He decided to raise her distress a notch or two.
“You always did have the nicest ass I’ve ever seen, you know that Jenny? So firm, so tight, so soft–it amazing actually. I’ve seen other women your age and they are all beginning to sag and droop. But not you, you have the ass of a twenty-year-old! An ass just ripe for fucking!”
“Ohh, God!”
He caressed her ass for another couple of moments before drawing his hand back. He waited as she tensed, expecting his swat and preparing for it. He waited until she began to relax, thinking he had changed his mind. He hadn’t.
SMACK! His large hand came down on her ass cheek in a stinging swat, sounding more like a gunshot than a spanking in the large hotel room.
“Yeeowch!”
Jenny squirmed on his lap trying to cool the burn as an angry red handprint appeared almost instantly on the pale flesh.
SMACK! Another hard swat on the other cheek gave her matching handprints on either ass cheek. He gave her four more swats, two on either side, until her ass was nice and pink over most of its surface.
He paused with each of these to let the effect sink in for her. When he stopped, Jenny lay there on his lap, her ass burning, but not daring to reach back to rub it.
“Now that we have your ass a very pretty shade of pink, we can get down to business!”
She couldn’t believe it–there was more to come! She groaned her disappointment but didn’t argue or struggle. She knew it would only make him angrier, and she’d get worse than a spanking.
A moment or two later he raised his hand and the main assault began; a rapid-fire barrage of swats one immediately after the other, alternating sides and placement to cover her entire ass with sharp stinging blows.
He didn’t give her any chance to catch a breath or even process one blow before the next one landed. Her squeals turned to screams as she rocked and twisted and squirmed on his lap trying to avoid or lessen the effect but nothing helped.
Then slowly there was something new… she began raising her ass up to the punishing hand! Her cries morphed into moans and groans of desire. And then the most incredible thing happened. She felt as if she needed to cum!
“Oh God Sir, please! Please, I need to cum! Please make me cum, Sir! Please, please make me cum!”
“You want to cum? Oh you really are a slut, aren’t you! Imagine cumming from a spanking! Is that it? Are you a slut Jenny? Are you my little fuckslut?”
“Yes! Oh yes, please! Please make your fuckslut cum! Oh God, please! Please, I’ll do anything… anything you ask, just, please! I need to cum so bad!”
“Oh my dear Jenny, you will do anything I ask whether I allow you to cum or not! But I do like to hear you beg, and so I will grant your request… in time!
“However, if you had been here when you were supposed to, you would have cum two or three times by now. Instead, you are wanting me to make you cum now and put off my own release even longer. I wasn’t the one who was late-do you think it’s fair that I should wait?”
“No, Sir.”
“Neither do I.” Instantly his hand shot out grabbing a handful of her long ink-black hair and pulled her down to her knees in front of him. “Now undress me!”
Startled by his sudden actions, she got right to work, unbuckling his belt and undoing the clasp of his pants. She pulled them down and gasped when she saw the bulge in his boxers that greeted her.
She had always been very impressed with the size of his cock–and the way it filled her lonely pussy and stretched her almost to the point of pain.
She had loved the feeling of him inside her from the very first time they’d had sex, and each time they got together was like that first time he opened her up. Jenny could feel her pussy salivating as it got ready to take the monster cock into its welcoming depths.
Hearing her gasp, he smiled. He was pretty proud of what he had to offer too, and her acknowledgment boosted his ego and confidence. He took a firmer grip on her hair and raised her face up to look at him.
“Now when you take off my shorts, remember what I told you about worshipping and honoring my cock.”
“Yes, Sir.”
He had taught her in some of their previous times together how he liked her to show her appreciation to the cock that pleased and pleasured her so much. She enjoyed it as well and knowing it pleased him turned her on. It made her feel more submissive and a little slutty too.
Jenny really looked forward to shedding her high-class socialite model image and getting down and dirty with him. He made her feel cheap, slutty, and whorish and she loved being “street” for him!
With a nod from him to continue, she pulled his boxers down using her shoulder for him to lean on as he stepped out of the garment. Jenny tossed it onto the pile with the rest of his clothes and turned to the object of her fantasies and lustful imaginings.
Before she was allowed to take the cock into her mouth she was taught she needed to pay some attention to it. She was taught to nuzzle it with her face, to rub her face against the cock and balls to wallow in his scent.
She was taught to kiss the tip lightly and kiss his balls as well as the source of the cum she so loved. She took the base of his cock in one hand and slapped her cheeks and lips with it and let the cock rest on her forehead for a moment.
Only after she had given proper reverence to his cock and his gave her permission was she allowed to begin taking it into her mouth…
