Spanking Stewardesses — Part 4


Now it’s time to play switcheroo. This will be my last post featuring this novel for a while. More will come in later posts.


Sharon dressed carefully for her date with Craig Jackson. To begin with, the tall, leggy stewardess selected a filmy pair of black nylon panties and a matching brassiere that made a striking contrast with her white skin. After careful consideration she rejected pantyhose in favor of regular length black nylon stockings held up by a black garter belt. Next, she selected a severe black dress that was fashionably short and ended about four inches above her knees. Finally, she put on her best pair of patent leather pumps which had spike heels and pointed toes.

She and Craig had been dating for several months, but the affair had not become serious until recently. As she waited for him to arrive, Sharon recalled how events had developed during the past couple of weeks. It had all begun at Craig’s apartment one evening when he playfully took her over his knee for a spanking. Although mildly humiliated and a little angry, Sharon had found the spanking quite exciting. As she sat on his lap afterward with her bottom tingling, they had petted much more ardently than they had ever done in the past and at times Sharon had been on the verge of losing her self-control. She could also see that Craig was thoroughly stimulated, and on several occasions she could barely refrain from clasping that obvious bulge in his trousers.


They had begun dating almost nightly after that, missing only those evenings when Sharon was out of town on flights. The spankings became a regular affair, and Sharon would do things to deliberately provoke him into spanking her. He never spanked too hard and always left her clothing in place. One evening they began to talk about the subject and, in a confessional mood, Sharon told him about the system she and her roommates employed to keep order in their apartment. Even though she blushed prettily, she described their system in detail and told him about the time she and Connie had been required to turn their bare bottoms up for twenty swats. Since she knew some of the details about Connie’s affair with Howard, she also told Craig about that—including the fact that Connie was spanked on the bare bottom.

In return, Craig made a confession that Sharon found quite startling at first. He had been raised by a discipline-minded spinster aunt in her thirties who had spanked him regularly during his teenage years! With some embarrassment he admitted that his aunt always prepared him herself, even when he was in his late teens, by making him stand in front of her while she unfastened and lowered his pants and undershorts. She always made him get over her knee for the hairbrush spanking, and he admitted that he could never sit down for hours after one of his aunt’s hairbrush workouts.

Although Sharon had overheard some of Kathy’s comments about discipline for the male, she had never taken her roommate seriously and had never considered paddling a fellow. However, Craig’s disclosures opened up the possibility and Sharon began to find the idea quite intriguing. On the past couple of dates, she had rather indirectly approached the idea of forming an equal partnership as far as spanking was concerned. Craig had seemed quite receptive to the idea, and she intended to pursue the subject further at the earliest opportunity.

A few minutes later, Craig arrived and they exchanged a light greeting kiss. Hand in hand, they walked to a nearby restaurant where they had eaten frequently and which had become their favorite rendezvous. As they were having dessert, Craig suggested seeing a play but Sharon gently demurred. Taking the hint, he suggested that they walk over to his apartment a few blocks away. As they walked to his place, Sharon could hardly wait for things to get started.

As soon as they arrived at the apartment, Sharon seated herself on the couch and crossed her pretty long legs provocatively. For once she didn’t bother to pull her skirt down and allowed it to hike up to the heavier parts of her nylons. She could feel herself blushing slightly as Craig couldn’t resist giving her shapely underpinnings an appreciative glance. He seated himself beside her and she pretended to be indifferent when he kissed her lightly on the lips.

“What’s the matter, hon?” he drew back, looking rather puzzled.

“Oh, nothing,” Sharon answered lightheartedly.

“Maybe I should warm you up a little!” he laughed, starting to pull her over his knees.

“No, wait!” Sharon pulled back, struggling to get free.

She had never offered any resistance in the past and Craig looked somewhat bewildered. “Wait for what?” he asked.

“There’s something I want to talk to you about,” she told him. In the brief struggle her dress had worked up even farther, revealing the heavier parts of her stockings and a couple of inches of bare white thigh as well as the supporters of her garter belt. She could see that Craig could hardly take his eyes off the eye-catching display, but did nothing to discourage his attentions.

“Go ahead,” he replied.

“Well, to make it short,” Sharon told him. “I think it’s about time we started taking turns warming each other up!”

From her comments on their previous dates, Craig was not surprised. “Well, that sounds fair enough!” he laughed, shrugging his shoulders.

“Does that mean you agree to go along with it?” Sharon asked. “After all, you’re bigger than I am and I can’t very well force you to. However, if you want to keep dating me, I think you’d better agree to be fair about it!”

“Okay!” Craig agreed. “I’ll go along with it!”

Sharon gave him a knowing smile. “Well, in that case, I want you to prove that you’re serious by letting me spank you exactly the way your aunt used to!”

Craig looked quite startled but made a quick recovery. “Don’t think I won’t get revenge later on!” he smiled.

“You’ll have good reason to!” Sharon assured him sweetly. “Now, let’s see. Your aunt always used a hairbrush, I understand. Do you have one?


“Well, bring it to me, little boy!” Sharon told him bossily.

As Craig departed from the room to get the hairbrush, Sharon uncrossed her legs and moved over to the center of the couch. She deliberately kept her skirt back over the tops of her black stockings, forming a provocative lap for him to lie across. When Craig returned in a moment carrying the hairbrush, Sharon quickly noticed the promising curve that was already developing in the front of his trousers. His eyes glued on her long tapering thighs, he handed her the hairbrush. It was an old fashioned brush made of wood rather than the modern plastic type that Sharon had been expecting.

“Now, stand here while I get you ready!” she told him with a knowing smile.

Sharon could barely conceal her amusement as she noticed that he was blushing furiously.

“You don’t really intend to…” he began.

“I told you that I was going to spank you exactly like your aunt used to!” Sharon reminded him with a smile. “And I do mean exactly, dear!”

Craig blushed even more hotly as Sharon unfastened his trousers and allowed them to drop to a ring around his ankles. His tight cotton shorts were bulging in front. Although she was blushing quite prettily herself, Sharon had no intention of turning back at this point.

“My, you’re naughty!” she scolded. “Tell me, did you get naughty like that when your aunt used to spank you?”

“Y-yes!” Craig admitted, looking somewhat shamefaced.

Sharon reached forward with both hands and began to pull the waistband of his shorts down. As the waistband caught in front on his erect penis, Sharon reached inside his shorts with her right hand and pulled his stiff member back out of the way. Craig tensed noticeably as her warm, feminine hand encircled his pulsating shaft. Continuing to hold his hard muscle in her right hand, Sharon used her other hand to work his shorts down to his ankles. Finally releasing his penis from her grip, she patted her nyloned thighs with both hands as a signal for him to stretch out over her attractive lap.

“Get over my lap, you naughty boy!” she told him with a knowing smile.

Hampered somewhat by the lowered trousers and shorts at his ankles, Craig managed to stretch out over her lap. As he lowered his weight against her thighs, both were very much aware of his erect penis pressing against her nylons. Deliberately taking her time to torment him, Sharon paused to tuck his shirttails up very carefully out of the way before reaching for the hairbrush. With a tongue-in-cheek smile, she pressed the back of the hairbrush lightly against his exposed buttocks.

“You’re going to get it but good!” she told him. “And I want you to prove to me that you can take it!”

She could see him anxiously tense his muscles as she lifted the hairbrush. Smack! Sharon brought the hairbrush down with a resounding slap on his right buttock.


“OW!” Craig jumped with surprise and pain.

“Hold still!” Sharon instructed bossily.

As Craig settled back down on her pretty lap, Sharon began putting the hairbrush to him with noisy smacks, first on one side and then the other. After he recovered from his initial surprise, Craig managed to endure the next few spanks rather quietly although he couldn’t avoid catching his breath and jerking slightly each time the brush landed on his exposed bottom. However, as his bottom began to turn pink from the hairbrushing, Craig could no longer hold still and was soon wriggling boyishly on her lap.

“Your bottom is getting red!” Sharon told him, thoroughly enjoying herself. “However, I’m not nearly through with you yet!”

As the pretty stewardess continued applying the brush to his reddening bottom, Craig was soon gasping for breath and squirming with each application of the brush. Sharon could feel his erect penis sliding back and forth on her nyloned thighs as he thrashed about on her lap.

“Hey, that’s enough!” he finally complained, looking back over his shoulders.

“You’re kidding!” Sharon laughed. “You’re going to have to be a lot redder than that before I’m through!”

She began smacking even harder with the brush, smiling as Craig jerked around on her lap. She could see that she was really beginning to get results, and carefully spread the spanks around his scarlet bottom.

“Ow! Ouch! Come on, that’s enough!” Craig could no longer conceal his reaction to the hairbrush spanks that left his bottom prickling and uncomfortably warm.

“Hold still!” Sharon demanded, quite pleased with the results.

“Ow! Please!” Craig continued to plead, twisting his smarting bottom away from her in an effort to avoid the stinging spanks.

“Come on! Stay in position!” Sharon told him. “Don’t be such a baby about it!”

Gasping breathlessly, Craig settled back down into position on her nyloned thighs. Sharon resumed with the hairbrush, covering his bottom with brisk smacks that made him squirm and swing his legs back and forth. It wasn’t long before he was blinking back tears and looking back over his shoulder to plead with her to stop.

“Please, stop! That’s enough! Ouch!” he implored.

“Your bottom is getting nice and red!” Sharon told him with a knowing smile.

The pretty brunette continued putting the hairbrush to his burning bottom, working up one side and down the other. Craig worked his hips frantically back and forth on her lap, his stiff member brushing against her cobwebby nylons. By the time Sharon finally brought the hairbrushing to a halt, Craig’s bottom was a flaming scarlet on both cheeks and he was in tears. As he got off her lap, she playfully rubbed the bristled side of the brush against his scarlet bottom.

Sharon had to laugh as Craig stood there in front of her tearfully rubbing his blazing bottom with both hands. Despite his obvious distress, his bulging and fully erect penis made it quite apparent that he had been thoroughly aroused by the discipline inflicted by the longlegged stewardess. As she watched him trying to rub some of the sting out of his bottom, Sharon made no effort to pull down her dress and left it up over the tops of her black stockings.

“You just wait!” he told her good naturedly. “Don’t think I’m going to let you get by with that!”

As Sharon watched, he began removing his clothing and was soon completely nude. Getting to her feet, Sharon grasped his hard lance with one hand and snuggled close to him.

“Why don’t we just forget about my spanking for the time being?” she smiled flirtatiously, using all her girlish charms to distract him. Her warm hand gently stroked his pulsating member. “There are so many other things we could do!”

“We’ll do those things later!” he told her.

Sharon’s lips formed a pretty pout and she released her grip on his penis. Craig sat down on the couch and lost no time pulling her face down over his lap. Sharon offered no resistance and soon found herself looking down at the carpet with her long legs stretched out on the couch. Craig promptly pulled her dress up in back, revealing an exciting gap of white flesh between the tops of her stockings and her black panties. Pulling the dress back to her waist, he gazed at her girlishly wide and rotund buttocks encased in the snugfitting panties. The wispy panties could barely contain all of her plump charms.

After a long pause, Craig reached for the waistband of her panties and slowly began drawing them down off her hips. Blushing beet red and keeping her eyes tightly closed, Sharon stifled an embarrassed gasp as she felt her pretty young buttocks being unveiled before his inspecting masculine eyes. She could just feel his eyes drinking in her feminine charms and her pretty gluteal muscles flexed as she shriveled with embarrassment.

“Lift your hips up a little, honey!” he told her. With a low moan, Sharon embarrassedly complied with the humbling order. As she raised herself just slightly off his lap, Craig pulled the panties down to completely expose her plump, rounded buttocks. Taking his time about it, he pulled the panties below the tops of her stockings where they would be completely out of the way. He left her black garter belt and stockings in place, allowing them to frame her pretty, quivering spanking surfaces.

The hairbrush was nearby on the couch, but Craig preferred the personal contact of his hand. Dropping his left forearm over her trim bare waist, he raised his right hand in the air and brought it down smartly against her right buttock. SMACK!


“Eeek!” Sharon uttered a girlish shriek as his capable palm smacked against her tender and yielding bottom. She squirmed on his lap, her feet flying up in the air.

Smack! Smack! Holding the longlegged young brunette firmly down on his lap, Craig began spanking her inviting bottom all over with his open hand. Sharon squealed with each spank, squirming prettily about on his naked lap and swinging her shapely nyloned legs back and forth. As she squirmed about, Craig could occasionally glimpse the enticing pink crevice surrounded by the curly patch of dark brown hair. Fully aware of how much she was exposing herself, Sharon blushed furiously but couldn’t keep her long legs together as the smarting spanks descended against both pretty bottom cheeks.

“Ow! Eeeekkk! Ouch! Please, stop! OW! Pleeeese!” Sharon yelped and pleaded as Craig’s palm continued to bounce up and down on her smarting and prickling bottom.

As Sharon’s sensitive buttocks began to smart and burn all over from the crisp smacks, the comely brunette couldn’t avoid kicking her long legs hard and wide as she thrashed about breathlessly on his lap. Craig couldn’t help staring at the display of inviting feminine charms and could barely refrain from slipping an exploratory finger into the pretty pink aperture at the fork of her legs.

“Ouch! Pleeeesee! Pleeeeeeeeeeeeeees!” Sharon pleaded, bursting into tears. “Please, stop! I can’t stand it any more! Please, it hurts something awful!”


As Craig’s hand continued warming her crimson nates, Sharon cried like a little girl and frantically tried to twist away from the burning spanks. Craig had originally planned to switch to the hairbrush at some stage of the proceedings, but found that the personal contact of his palm on her velvety soft buttocks was more tempting. He applied each spank with care, allowing his palm and fingers to rest in place for a moment afterward.

“Pleeeeeeeese! Pleeeeeeeese!” Sharon shrieked hoarsely, kicking the couch with her pointed heels as she frantically kicked her pretty legs up and down. “Pleeeeease! I’m just burning up!”

Craig didn’t stop until Sharon’s girlishly plump buttocks were fire red on both cheeks, and the pretty stewardess was sobbing and tearfully pleading with him to stop. When he finally relaxed his grip on her, Sharon jumped to her feet and frantically began rubbing her red bottom with both hands. After a moment she recovered her composure somewhat and, her eyes fastened on his erect penis, began removing her clothing. Craig watched appreciatively as the long-legged brunette removed everything but her garter belt and black stockings.

Blushing quite prettily but making no effort to cover herself up, Sharon stood there for a moment as he stared at her full, rose tipped breasts and the intriguing triangle of dark brown hair at the top of her legs.

“Come here, honey!” he told her quietly.

Looking delightfully embarrassed, Sharon padded over to him in her stocking feet. Cupping his hands gently around her stinging bottom, he gradually pulled her closer to him and pressed his face into the inviting patch of hair. The area was already a little damp and sticky.

“Ooooh!” Sharon trembled as he worked his face down between her legs, his mouth pressed against the warm lips of her vulva. “Perhaps we could both…”

She watched eagerly as Craig stretched out on his back on the couch. Leaving on her garter belt and hose, Sharon knelt over him with her knees next to his shoulders and leaned forward on her hands and elbows. Looking up into the pretty nest of dark brown hair, Craig quickly raised his head from the couch and began licking the pink cleft. Feeling a masculine tongue caressing her most sensitive parts, Sharon squirmed with delight and lowered her weight against him. His nose between the crevice of her scarlet buttocks, he began licking her moist charms.

As she lowered herself over him, Sharon found her pretty face next to his bulging and pulsating member. Opening her mouth, she slid her tongue gently over the crown of his sturdy shaft, feeling his entire body tense with pleasure at the intimate caress. Continuing to flick his throbbing penis as if it were an ice cream cone, Sharon worked her hands under his hips and dug her fingernails lightly into his buttocks. As she suspected, he was still quite sensitive from the hairbrush spanking she had administered, and his body stiffened as she tormented him by scraping his hips lightly with her nails.

In response, he worked his tongue between the outer lips of her vulva, caressing her most intimate parts. Sharon wriggled with girlish delight atop him, bathing his face with her warm feminine fluids and leaving him completely drenched. As he worked his tongue against her clitoris, the squishing and slurping sounds were quite audible. Sharon began moving her pelvis back and forth, brushing her wet cunny all over his face.

Resting her chin on his stomach, Sharon opened her pretty mouth as far as she could and gradually began working his pulsing member into her mouth. Craig coiled with tension under her as he felt her moist and warm mouth surrounding his bone hard shaft. Sharon inserted it very slowly, constantly nibbling with her lips as she did so. Even though it forced her jaws apart almost uncomfortably, Sharon worked the big head between her teeth and began to see how far she could get it into her mouth. By slowly becoming accustomed to having more and more of it in her mouth, she finally managed to work it in nearly to the back of her mouth.

Feeling his stiff member plunged deeply into Sharon’s pretty mouth, Craig employed his fingers to spread the cheeks of her bottom apart and began running his tongue up and down the full length of her split. Feeling a masculine tongue tormenting her pink anus, Sharon twisted violently and gulped heavily on his throbbing penis. She began sucking on it with audible gulps, continuing to torment his sensitive hips with her fingernails. Thoroughly lubricated by her saliva, his slippery penis slid back and forth in her mouth.

After caressing the valley between her buttocks with his tongue, Craig returned to the coral opening of her vulva. As he once again worked his tongue between the outer lips, Sharon’s moisture covered his face and forced him to swallow her fluids. She gave a frantic jerk as his tongue once again found her clitoris, and lowered her weight completely on his face.

Breathlessly sliding her mouth back and forth on his aching penis, Sharon could feel the tension building up inside him as he held himself back as much as possible. Caressing her scarlet buttocks with his hands, Craig began concentrating almost entirely on her highly sensitive clitoris, flicking it repeatedly with his tongue. Squirming frantically around on his face, Sharon began to lose her self-control completely. Drenching his face in her moisture, she shuddered violently and suddenly reached a quivering orgasm. Moaning and tossing, she squirmed about on top of him.

Craig could hold himself back no longer and, with a sudden jerk of his pelvis, sent his climax gushing into her throat. Sharon instinctively started to pull away, but quickly changed her mind and took the warm, sticky spurts in her mouth. As she gulped and swallowed hard, she could feel Craig’s tongue once again traveling the full length of her split.


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