The Romance of Chastisement

The Romance of Chastisement

Friday, December 30, 2011

Palm Springs Pt 1

This time of year I get to thinking about someplace warm...someplace like Palm Springs.

Paul found it frustrating that they checked his ID so closely. He sighed. The problem was, he looked so young. And he knew it. His blonde hair that tended toward curly, his cherubic face (yes, girls had called him that), his slender build (he was a runner), all made him look like he was 16, not 21. So he stewed as he sat in the bar at the hotel where he'd come for a long weekend while the bartender poured over the ID. All his other friends were still in bed. Here he was up at the crack of noon.

"Problem over there?" Paul turned to see who had spoken. It was a thirty-something woman who was sidling up to the bar. She was a looker too. A busty brunette with great long legs in a tight dress, she looked to be around thirty-five or so. Paul's mind began to race. What have we here? A cougar? A lonely divorcee?

"They don't think I'm 21," he said with a wan smile.

"You do look young," she admitted. "But," she said, pulling back and giving him the once over, "you look fit."

"Thanks," said Paul. "I run."

"Ah, now that explains it." They struck up a conversation. Mostly she asked Paul about himself. He explained that he was a senior at Redwood State, here on break, just cutting loose. He told her about his major, his work in drama. That got her interest. "You act, do you?" Paul admitted he did. "How interesting...mmm, better and better," she said.  She asked if he had a girlfriend. He explained that no, not presently, but not for lack of trying.

There was a lull in the conversation, and she looked to be thinking about something, while regarding Paul intently. "Look, Paul" she said finally, "do you want to make some money?"

That was unexpected. He'd hoped she was going to suggest they head for her room. She was hot and Paul was feeling charged up by the attention. So what if she was fifteen years older? He'd heard stories from his friends about being picked up by cougars, older women who wanted it from young guys. Maybe this was it. "Um, sure, uh, what's the deal?"

"Let's get a booth," she said. "By the way, I'm Tessara Trask. Call me Tessa." As she led the way to a private booth where they could talk, Paul marveled at the finely toned legs and the side to side sway of her hips. The tight skirt displayed her taut rounded buttocks. Paul's penis surged at the sight. Once seated, she leaned toward Paul. "I provide a rather unique service and my last partner, well, he left. You see, this is Palm Springs. There is a large and rather wealthy retirement population here and a market has arisen for, shall we say, entertainment services of a rather intimate nature."

Paul stared. What was she suggesting?

"It sounds mysterious, but what it amounts to is that many of these people who are my clients like to just watch while I present certain tableaux for their pleasure. All of them are women. I don't do shows for men. And, my clientele have very interesting tastes. Do you see?"

No, Paul didn't see. She was talking around it. "What exactly is it? What is this intimate entertainment?" He was interested, though. This sounded exotic.

"Very simply, I have a clientele that will pay substantially to witness the live enactment of a scene featuring a boy, such as yourself, being well... disciplined for various misdeeds." She let that sink in. "It would be worth $500 for each scene you did."

Disciplined? And did she say $500 a pop?

"You have the look that they like," Tessa continued, "youthful, boyish, slender---you're almost pretty." She touched his hair, brushing it away from his forehead. "Yes, they'd like you a lot."

Her touch was electric and Paul was taken aback. "What do you do exactly?"

Tessa shrugged. "A little role play. Maybe I'm your tutor, or governess and you've been unruly, disobedient. I punish you while they watch."

"Punish how?" asked Paul. This had slipped into a bizarre territory.

"Oh, I scold you for your misbehavior, then perhaps a brisk spanking...things like that. They like to see cute boys like you get spanked," she added, smiling.

Paul sat back, thinking. He felt all hot and cold at the same time as he felt Tessa's eyes on him. His penis twitched again. "A spanking?"

"That's right," said Tessa. "Just like mommy." She grinned like the Cheshire Cat.

"The, uh, spanking part, that's just pretend right?"

Tessa cocked her head and smiled. "Come on, honey, they're paying you good money. You have to make it real for them. Anyway so what? You're a runner, right? Long distance. Don't they say no pain no gain? Wouldn't a little discomfort be worth $500?"

Paul knew it was crazy but the money was just too alluring. And part of it was Tessa---she was hot. And no doubt, experienced. His fantasies started to run riot. He said he'd give it a try. Tessa was elated. "Good boy," she said, giving his cheek a pinch. Paul hated it when girls did that, but somehow with Tessa it seemed ok. "Come on then. We need to go shopping."

Paul found it easy to slip into the role of the young male escort and let Tessa lead. She was naturally dominant and Paul, without a whole lot of experience with females, felt pliable and obedient. "Oh, you are such a gentleman," she cooed as he opened doors for her and carried packages. To the rest of the world it must have looked as if he were a favorite nephew out on a shopping trip with his aunt. She bought him tailored grey shorts---a size or two too small. It felt ridiculous the way they rode up his thighs and were tight across his bottom. She said he needed white dress shirts, a tie and a blue blazer. Next came pajamas---little boy style. The right underwear was also needed she said-tighty-whities and undershirts.

She decked Paul out in grey pants with a white shirt and blue tie. Then she took dirt and smeared it all over the white shirt.

"What did you do that for?" asked Paul.

"You'll see. We're going to see Mrs Murphy. She was a preacher's daughter before she married her rich husband, now deceased, of course. It's this scene she witnessed 60 years ago." The little red convertible tooled along Frank Sinatra Drive. "You are James. He has been told to get ready for church, but instead he went out and played in the dirt. Just follow my lead. It's theater. We make it up as we go." The car pulled up to a gated community. Tessa punched in a code and the car proceeded through. She turned into the circular drive of a large, well appointed home. "This is it. Remember, follow my lead. You are about 14 years old. Use your extemporaneous acting skills."

They walked up and rang the door. A stout woman in her sixties answered. Her eyes lit up when she saw Paul.

"Hello, Mrs Murphy. I wonder if we could come in." She smiled a knowing smile and ushered the pair in. "We were on our way to church. I explicitly told James here to stay clean once he was dressed for church and do you see what he did? He started playing ball and got dirty." Paul got it. He was a naughty kid who had gotten dirty in his church clothes and had made his mother angry.

Mrs Murphy said with a shine in her eyes, "Oh my. How naughty. You'll have to clean him up, then."

"Yes," said Tessa. "How disgusting. The very idea. Look at him. Can we use your bath?"

"Why, yes, it's right upstairs. Imagine. The young scamp. I suppose you will punish him too?" Mrs Murphy's expression was bright with excitement.

"Oh you can be sure of that," said Tessa, slipping into the role of an irate mother. "Come along James." Tessa grabbed Paul by the earlobe and pulled him down a hallway toward the stairs. Paul winced but allowed Tessa to pull him along. It hurt to have her yank on his ear like that. It actually did remind him of his mom when she was bent on teaching him a lesson. They climbed the stairs and Paul winced as Tessa tugged him along.

"Ow...ow," he said as Tessa led him down a hallway. They entered a large bathroom.

"Now you stand right there while I draw a bath," said Tessa, turning on spigots. "In fact, you can just take those dirty clothes right off." Mrs Murphy watched gleefully while Paul stripped down to his underwear. Somehow he couldn't bring himself to remove this last veil of modesty even though he knew that was what was expected of him. It was pretty embarrassing to strip down in front of two fully clothed women.

Tessa turned around and spoke sharply. "Well? I said take off your clothes. All of them, young man. Right now." She eyed him sternly.

Paul grimaced. He knew she was acting, but still, her tone sent a shiver down his spine. Ok, if this is what it took. He slid his shirt over his head, then he glanced at Mrs Murphy. Her eyes were glued to his groin. He slid his underwear down and let them drop to his ankles. She smiled approvingly. Paul got in the tub. Tessa started washing him with a washcloth. "Now, we'll get you cleaned up, you dirty scamp," she said. She soaped him up and scrubbed him like he was a four year old. Then Paul felt her fingers underneath the water, massaging his penis. It leapt to life, growing hard under her ministrations. Paul blushed. He couldn't control it.

"All right, stand up," said Tessa. Paul stood slowly, willing his cock to soften. It wouldn't.

"Well, Mrs Murphy, would you look at that!" Paul's cock stood straight out proudly. Tessa glared at Paul. "Just what is that?" she said.

"I---I can't help it, er, ma'am. It just happened." Paul tried to cover up. Geez, this was embarrassing.

"You can just get yourself right out of this tub." Paul got up, dripping wet. Tessa toweled him off while at the same time talking to Mrs Murphy. "Do you see that?" she said indicating Paul's rampant penis. "If this boy didn't need to be punished before, he certainly needs it now. Might I borrow your hairbrush to teach this naughty boy a good lesson?"

"Oh, yes," said Mrs Murphy gleefully. "It's right in the bedroom."

Tessa grasped Paul by his stiff appendage and pulled him along, heading down the hall to the bedroom. Paul allowed himself to be led, little jolts of pleasure vying with acute embarrassment. Tessa sat down on a vanity bench and made Paul stand to her right.

"Now, James. You are going to be punished. Imagine! I told you to behave while we got ready for church and instead you played in the dirt. And on top of that you have the impudence to sprout....well, you know, an erection....while I'm trying to get you clean."

"I think he deserves a most sound punishment, don't you Mrs Murphy?"

"Indeed I do," said Mrs Murphy enthusiastically.

"I'm going to put James across my knee, Mrs Murphy. I think he deserves a very sound spanking."

"By all means," said Mrs Murphy. Her eyes were practically shining with anticipation.

Paul's eyes widened as Tessa pulled her dress back to reveal bare thighs. She tugged Paul and he fell across her lap. He felt a distinctly erotic tingle as his stiff penis contacted Tessa's thighs. She edged her legs apart just a bit and his penis slid between them. He felt another surge as she clamped them shut. Now her hand was resting on his bottom. She squeezed and patted both cheeks. Mrs Murphy was practically licking her lips.

"Look at this naughty bottom," said Tessa. "What an impudent little fanny James has. Just made for applying correction, wouldn't you say?"

"Oh yes," said Mrs Murphy. She leaned forward so as to not miss a thing.

"Well I intend to teach him a lesson. I'm going to set this little bottom on fire." Paul squirmed under the ministrations of her hand which was still patting and stroking his bare hind cheeks. He hoped this wouldn't hurt too much. "Naughty boys. They need a good spanking now and then, Mrs Murphy."

"Oh I couldn't agree more, dear," said the matronly lady, obviously excited now. "You go right ahead."

Paul felt her hand leave. For a moment there was only a cool breeze tickling his bare cheeks then splat! Tessa's hand impacted his left cheek. It was a shock. Then her hand smacked his right cheek. She started spanking him at a measured pace, smacking one cheek then the other alternately. It tingled at first, but then started to sting. The smacks rang out in the bedroom and Paul shifted, trying to alleviate the spreading sting. Ouch! This was starting to burn, he thought. Tessa kept on delivering steady crisp spanks that made him jerk in response. At the same time she kept up a running line of scolding.

"Just think (smack! smack!). I leave you (smack!) alone and you play in the dirt (smack! crack!). How many times have I told you (smack! crack! splat!). I'm going to spank this little fanny until it glows, do you hear? (smack! crack smack!). You will learn to obey me! (smack! crack!)

Ow! Yow! This was really stinging! Tessa's hand smacked steadily. Paul squirmed under the onslaught.

She stopped for a moment and let her hand remain on Paul's buttocks, rubbing and patting. His erection returned. The relief was short-lived.

"Mrs Murphy, will you hand me your hairbrush?"

"Certainly, dear," said the matronly Mrs Murphy, handing her a stout flat-backed wooden hairbrush.

"All right, James. We will now get to the seat of the problem." Paul cringed as she tapped his bottom with the wooden brush. It felt hard and unforgiving. How much was this going to hurt?

He soon found out as the hairbrush spanks began to fall with a sharp smack! Smack! Smack!

"Yow! Oww! Owww!" Paul started to yelp. His legs flutter kicked.  Crack! Crack! "Ow....ow...ouch...Please ma'am, I'll  be good." It didn't require much acting to play the pleading little boy. This spanking was the real thing. His ass was on fire. He looked at Mrs Murphy who was on the edge of her seat, transfixed, it seemed, by the mother-son disciplinary drama being played out. The spanks with the hairbrush hurt lots more than her hand.

How long was she going to spank him? This was getting to be really painful. Each smack stung atrociously. His eyes were starting to water as Tessa continued to smack his bottom briskly, harder now and faster, it seemed. He arched his back and let out a long wail. Just when it seemed unbearable she stopped. She handed the brush back to Mrs Murphy and rubbed and kneaded his bottom. He slumped over her lap. As she rubbed his erection returned.

"Up with you now," she said, cracking his red behind a final time. "Now you stand over there, nose to the wall."

Paul got to his feet. His hands went back to rub his inflamed cheeks. His erection bobbed up and down.

"Well, I think he's been taught a good lesson, don't you Mrs Murphy?"

"Oh, yes," said Mrs Murphy. "A sound spanking for a naughty boy. It was exactly what he needed." She smiled broadly as she gazed at Paul's totally red and swollen bottom, twitching and flexing as he tried to stand still as commanded.

"Turn around James. Look," said Tessa. "The impudent boy still flaunts his maleness." She put her hands on her hips. "I think we should do something about that," she said. "Come here, James."

Paul hobbled over to her, clutching his bottom and rubbing furiously. He made hissing sounds as he sucked air through his teeth in reaction to the horrible sting from the hairbrush. He stood next to her, his penis bobbing. She told Paul to sit on her lap. "Now will you behave? She said gently. Paul nodded, "yes, ma'am." The feeling of his hot buttocks sitting on Tessa's lap made his cock stand straight up. She reached down and touched it with her hand. The touch turned to stroking. Mrs Murphy's eyes were wide with excitement as she watched Tessa stroke Paul's erection. He began to move his hips, pumping in time with Tessa's stroking. Finally he could stand no more and his body went absolutely rigid as he pumped his seed in great jutting arcs into a towel in Tessa's left hand.


"She likes to see them cum," said Tessa, as they drove back into Palm Springs downtown. "I don't know why. It's probably a fantasy or some remembered incident from long ago." She parked at the hotel and fished a wad of cash out of her purse. "Here it is, $500." He took the money.

"Call you again?"

Paul winced. A stew of emotions boiled inside. His bottom still throbbed, but he had regained his erection. Just being next to Tessa in the car thinking about what she had done-the nudity, his vulnerability---and that lush body of hers. "Ok,' he said.


She called a few days later. She met him at a different hotel, the Desert Springs in Palm Desert. She had a girl with her. No, she was a woman in her twenties but she looked young.

"This is Becky," she said. Paul said hello. She was cute. Chestnut hair fell to below her shoulders framing a pretty face with dainty features.
Tessa explained. "Some of my clients like scenes with girls too. Today we're going to see Mrs Smith. Not her real name of course, but Mrs Smith has a certain fondness for school scenes. She has a room in her house that she has furnished with desks and a blackboard, some props she picked up." Paul was instructed to dress in slacks and a shirt with a tie. Becky wore a pleated skirt, a white blouse and bobby sox with loafers. We look like we should be on the set of "Happy Days" thought Paul.

It was an imposing house set well back from the road. They parked in the circular driveway. "Remember, kids, you are teenagers and not too well behaved ones at that. Becky, I know you like this scene. Paul, this will be a bit more intense but there will be extra. Are you ok with this?"

Paul nodded but he gulped. A bit more intense? What did that mean? But it was too late to reconsider. They had arrived. It was showtime.