I’m going a little out of order here, but it really makes no difference since these chapters are almost self contained. Now we are back to the M/F scenes.
“As far as I’m concerned, you’re both going to get it!” Howard spoke sharply to Connie and Gloria.
For the past several weeks, Connie had been spending considerably more time at Howard’s apartment than at her own. As a result, she had become good friends with Howard’s pretty teenage daughter, Gloria. Nearly eighteen, Gloria was a well developed brunette with a vivacious personality. At 5’7” she was already several inches taller than Connie, and often kidded her future stepmother about it.
“Please, Howard, I-I think we can explain…” Connie stammered as she and Gloria looked at one another in alarm. Gloria was aware that Howard disciplined Connie in the same manner that he had always employed with her, and had often teased Connie about it. However, Howard had never threatened to punish them both at the same time before.
“Yes, daddy, I….” Gloria tried to explain.
Howard shifted through the bills and shook his head. Some time ago, the two young women had gone on a shopping trip to obtain some hew clothes for Gloria. However, they had gone well beyond the monetary limitation specified by Howard. Moreover, in going through the bills Howard realized that some of the items purchased had been clearly unnecessary.
“Well, I’m waiting!” Howard remarked, looking from one to the other.
“Well… uh…” Connie felt her cheeks grow hot.
“Daddy, we…” Gloria began, but couldn’t find the words to continue. She had known for some time that she would have to pay the penalty for the shopping spree, but had been hoping that her father would let her off lightly.
“The fact is that neither one of you has an explanation,” he told them. “I’m going to punish you both right now!”
Connie gulped and blushed warmly, while Gloria bit her lip and looked anxiously at her father.
“Gloria, go and change!” Howard told his daughter.
Gloria’s knees buckled slightly. “No, daddy, not that!” she burst out.
“Hurry up!” he told her.
“But not in front of her!” Gloria continued to protest, her face quite red.
Howard put his hands on his hips and glared at her. “If you keep stalling, it’s only going to be worse!” he warned her.
“But, please, daddy,” Gloria pleaded. “It makes me feel so… so… juvenile!”
“That’s the idea!” Howard reminded her. “Now hurry up!”
Blushing furiously and looking quite distressed, Gloria departed from the study. Connie, who had been rather mystified by the conversation, looked anxiously at Howard.
“Please, Howard!” she appealed. “Don’t punish me in front of Gloria! It would be humiliating!”
Howard looked severely at her. The pretty blonde was wearing a fashionably short blue frock that made her appear all the more youthful, dark nylons and spike heels.
“No, you two got into this together, and you’re going to pay the penalty together!” he told her. “It’s too bad you don’t have a punishment uniform to wear the same as Gloria!”
Connie looked both uneasy and curious. “What do you mean?” she asked nervously.
“You’ll see when Gloria comes back!” he told her.
Connie watched apprehensively as he brought out the black leather razor strap and placed it on top of his desk. The strap had obviously been oiled quite recently, and Connie swallowed hard at the sight of the gleaming black leather. Next, Howard pulled a plain chair out to the middle of the room. Waiting for Gloria’s return, he seated himself behind his desk and went through some papers, deliberately ignoring Connie’s presence. Given no choice, Connie simply stood there anxiously shifting her weight from one foot to the other, biting her lip and hoping that Howard would pay some attention to her.
It was several minutes before Gloria returned, crimson with shame and head hanging. The leggy teenager was attired in her standard punishment uniform consisting of trim fitting, long sleeved white blouse worn without a brassiere beneath it, a little bright red flared skirt that barely covered her hips and failed to completely conceal her pink panties, a pink garter belt that held up regular length nylon stockings and white pumps with three-inch heels. In addition, she wore a large red hair ribbon in her dark brown hair.
Connie gasped with astonishment as Gloria made her blushing entrance, tugging self-consciously at the hem of her abbreviated skirt. Despite her embarrassment, there was nothing the pretty teenager could do to conceal her stocking tops, bare white thighs and garter belt suspenders. Moreover, with each step she took, a glimpse of her pink panties came on display both in front and back.
“Please don’t look at me!” Gloria glanced embarrassedly at Connie. “It’s too embarrassing!”
However, Connie was too dumbfounded at the sight to take her eyes off Gloria. She quickly noted the absence of a brassiere and watched as Gloria’s well developed young breasts jounced noticeably with each step. Howard arose from behind his desk and looked his blushing daughter over carefully.
“I see you haven’t forgotten anything!” he told her. “Now, stand right in the center of the room!”
Her eyes riveted on the carpet, the scantily attired teenager obeyed.
“Stand beside her, Connie!” Howard directed.
Connie rather apprehensively obeyed, blushing and keeping her eyes averted except for occasional darting glances at Howard. He looked the two miscreants over carefully.
“Connie, you see how Gloria is dressed. At future sessions, you will wear exactly the same type of uniform!” he spoke up.
Howard!” Connie gasped, her knees weak under her. “I couldn’t! I just couldn’t!”
“In fact,” he went on, ignoring her outburst. “As soon as we’re finished here, I want you to get into such an outfit right away! You can probably borrow a few things from Gloria.”
“Howard, please!” Connie stammered. “I-I couldn’t parade around like that!”
“For the time being,” Howard went on, continuing to ignore her pleas. “We’ll have to get by with a makeshift costume. Roll your dress up to your hips!”
“Howard!” Connie sounded desperate.
“Quit stalling!” he ordered her.
“Ooooh!” Connie moaned with despair and reaching down with both hands, began rolling her blue dress up slowly. Howard watched carefully as her dark stocking tops came into view. Blushing hotly, Connie slowly pulled the dress up over her bare white thighs.
“Roll it very tightly and hold it there!” Howard instructed the red-faced young woman.
Tears of shame filmed in Connie’s eyes as she stood there meekly holding her dress up in the required manner. Observing the two pairs of pretty stockinged legs appreciatively, Howard seated himself on the plain wooden chair. Spreading his thighs apart, he looked at the two anxious miscreants.
“Come here, Gloria!” he ordered.
“Please, daddy!” Gloria pleaded in a small voice as she slowly walked to him with obvious reluctance.
While Connie watched with some concern, Howard grasped the leggy teenager and pulled her face down over his lap. Her abbreviated skirt rode up in back, revealing her plump, pantie-clad bottom. The panties barely covered the two mounds of soft flesh, which quivered anxiously as Howard turned the short skirt up inside out. After a pause, Howard began peeling the panties down with deliberate slowness.
“Please, don’t bare me in front of Connie!” Gloria pleaded with obvious distress, looking back over her shoulder at her father.
Paying no attention to her pleas, Howard continued drawing the panties back. Gloria gasped and shuddered with embarrassment as her pretty girlish mounds came into view. Howard pulled the panties down inside out, lowering them below the tops of her stockings. Her pink garter belt and brown stockings were left in place. Her face scarlet with shame, Gloria held her long legs tightly together.
“Please, don’t look at me, Connie!” she pleaded. “It’s… it’s shameful!”
Despite Gloria’s earnest pleas, however, Connie couldn’t take her eyes off the sight of the mature young woman stretched out over her father’s knees with her panties at half-mast. In fact, Connie was so absorbed by the spectacle that she allowed her dress to slide down a little in front.
“Keep your dress up, Connie!” Howard corrected her. “Show your panties!”
Feeling her cheeks grow quite hot, the pretty blonde haplessly rolled her dress up again, holding it in place with both hands. Howard nodded approvingly as he looked at her dark stocking tops, plump bare thighs and the glimpse of white pantie that was barely visible.
“Now keep it there!” he admonished her.
Turning his attention to Gloria, he dropped his left forearm down over the small of her back to hold her in place. Raising his right hand, he brought it down lightly on his daughter’s pretty white right buttocks. Gloria gasped and swung a foot upward, wriggling with shame as he familiarly left his hand in place for a moment afterward. Remembering to hold her dress up, Connie watched with both fear and fascination.
Howard raised his hand and this time applied a light slap to Gloria’s left cheek, once again letting his hand rest in place for a moment afterward. Gloria squirmed prettily but obviously more from embarrassment than discomfort.
“Oooh!” the pretty teenager moaned softly, keeping her blushing face turned away from Connie.
As Connie watched closely, Howard set about administering a light hand spanking to Gloria’s pretty nates. Taking his time, he covered both bottom cheeks with light but noisy smacks. After about twenty spanks, Gloria’s rounded bottom was a pretty shade of pink all over. The cute teenager was crying with mortification and swinging her stocking legs back and forth. Howard paused and took a long look at his handiwork.
“Now, stand up!” he directed Gloria. “But keep your panties down and hold your skirt up!”
Gloria tearfully got to her feet, making no effort to pull up her panties. Looking quite shamefaced, she obediently held the skirt up in back, exposing her pink bottom. The skirt was so short in front that a patch of dark brown hair was clearly visible despite her efforts to preserve her modesty.
“Come here, Connie!” Howard commanded the petite stewardess. “And don’t let your dress down!”
Connie, who hadn’t been expecting her turn to come so quickly, buckled slightly at the knee and slowly began walking over to Howard. Holding her dress up to her panties, she felt horribly self-conscious and could barely hold back the tears.
“Please, Howard, couldn’t you punish me privately?” she pleaded, looking at him imploringly.
Scarlet with shame and keeping her eyes tightly closed, Connie allowed herself to be pulled face down over Howard’s capable lap. While Gloria watched with great interest, her father pulled back the blue dress to reveal Connie’s prettily rounded bottom encased in the skinfitting white nylon panties. Despite her own agitation, the pretty teenager could barely suppress a smile as Howard inserted his fingers into the waistband of Connie’s panties.
“Oh, don’t, please!” Connie wailed, nearly in tears. “Not in front of Gloria, please!”
As Connie continued to plead, Howard gently slipped down her panties, his fingers pressing lightly against her most intimate areas. As her full, rounded buttocks came into view, Connie stifled a sob and shriveled with embarrassment as she felt the others’ eyes glued on her upturned buttocks. As he had done with Gloria, Howard pulled the panties down inside out below the tops of her dark nylons.
“Ooooh!” Connie moaned and began to cry softly with shame at having her panties ignominiously pulled down inside out around her knees.
Smack! Howard smacked her right cheek lightly with his open palm, letting it rest familiarly in place for a few moments afterward. Connie threw back her blonde head and her feet jerked upward.
“Ow!” she gasped. “Please don’t spank me in front of her! Please, don’t!”
As Gloria watched with great interest, Howard proceeded to give Connie a light warm-up spanking. As her comely bottom turned a healthy pink on both cheeks, the attractive stewardess squirmed about girlishly on Howard’s lap and swung her pretty legs back and forth. From time to time, she unavoidably exposed the pink charms between her legs. By the time her bottom had endured twenty noisy slaps, Connie was crying and breathless.
“All right,” Howard finally announced. “Now I want both of you to bend over the front of the desk there! Be sure and keep your bottoms bare!”
Howard watched as the two victims anxiously assumed the position with Connie stationed on Gloria’s left. In a moment, the two apprehensive young women were bending over the top of the desk with their elbows and forearms resting on the desk top and their pink bottoms jutting out invitingly in back. Their panties had fallen to their ankles, leaving an unimpeded view of their shapely, stocking-clad legs. As Howard paused for a few moments to appreciate the scenery, the two miscreants shuddered at the sight of the black leather razor strap right in front of their eyes.
After making them wait anxiously for a couple of minutes, Howard got up and picked up the razor strap. “Since you both got in this together,” he told them. “I think that it’s appropriate that you get punished together. Now, keep your bottoms sticking out just like that!”
With the strap dangling right behind them, both young women couldn’t help puckering and squirming at the prospect of a good hot spanking. Both were crying softly and hoping it would soon be over with. Looking at the two squirming targets appreciatively, Howard stepped behind Connie and firmed up his grip on the strap. Splat!
“OWWWW!” Connie screeched, nearly straightening up as the well-oiled strap smacked across both cheeks of her upturned bottom with a fiery kiss.
“Eeeeek!” Gloria squealed just as loud as Howard applied the second stroke to her unprotected bottom.
“Stay in position, girls!” Howard reminded them, watching as the two tearful young women settled back into position on the desk.
“OWW! Oh, my! Please!” Connie screamed as the second stroke of the strap smacked against the tender bases of her buttocks.
“Oww! Daddy, please!” Gloria shrilled, twisting her cute posterior furiously as the strap smacked hotly against both bottom cheeks.
Walking up and down behind the two young women, Howard applied the strap alternately to their bottoms. Screaming and crying and pleading for mercy, Connie and Gloria twisted and shimmied their reddening bottoms frantically as the strap set them afire. Both stamped spike heels repeatedly against the carpet, and would have kicked their pretty legs much more had it not been for the lowered panties around their ankles.
“Owwww! Pleeeeeese! I can’t stand it!” Connie shrieked, her knees sagging weakly under her.
“Daddy, stop! Pleeeeese! Pleeeeeees!” Gloria pleaded between sobs.
Splat! Splat! Ignoring their fervent pleas, Howard continued applying the strap to their scarlet and blistering bottoms. Applying the strap with practiced skill, he made certain that no sensitive nerve was left untouched and concentrated on the extremely tender flesh at the base of their bottoms.
“Owwwwww! Pleeeeeese! Pleeeeeeeeese!” the two hapless victims pleaded in unison.
Splat! Splat! Howard continued applying the strap until both Connie and Gloria had broken down completely and were sagging weakly over the desk top, blubbering like babies with their red and blistered bottoms sticking up together.
“Now stay there for five minutes!” Howard ordered them. “And don’t rub your bottoms either!”
Sobbing heavily, Connie and Gloria meekly remained in position as Howard returned the strap to the closet. Sitting down a few feet away from them, Howard leaned back to observe their scarlet buttocks and prettily displayed legs.
“All right, Gloria, you can go now!” he finally announced. “However, Connie, you remain in position!”
Gloria slowly straightened up and reached down to pull up her panties. Gently rubbing her burning bottom, the tearful teenager quickly left the room and closed the door behind her. As soon as she had departed, Howard got to his feet and dropped to one knee behind Connie. Lifting her pretty feet one at a time, he extracted her panties from her ankles and stuffed them into his pocket.
“Please, Howard, you’re not going to spank me any more?” she tearfully pleaded in a desperate tone. “Please, I couldn’t stand it! Please, honey, I’m just blistered all over!”
“No, I’m not going to spank you,” Howard replied. “Now spread your feet apart!”
“Well, what are you going to do?” Connie asked, apprehensively spreading her feet apart as he requested. Realizing how much she was exposing herself, she blushed hotly. When Howard did not reply, the comely stewardess suddenly began to catch on as to what he had in mind.
“OH NO!” Connie screeched. “YOU WOULDN’T! No, don’t! Please! Oh, no, anything but that!”
Twisting her red bottom to one side, she looked up desperately over her shoulder. With an alarmed gasp, she noticed that Howard’s fully erect penis was already out of his trousers!
“NO, HOWIE, NO!” the pretty blonde shrieked. “I couldn’t stand it! I just couldn’t! Please, honey, anything else! Oh, for God’s sake, please!”
“Stay in position!” he demanded, ignoring her entreaties. “I’m going to use plenty of vaseline!”
Crying and shaking, Connie leaned forward with her elbows on the desk and her scarlet bottom jutting out vulnerably in back. Howard brought a jar of vaseline from the closet and dabbed it generously between the crevice of Connie’s cute behind. Connie squirmed with shame and fear as she felt him lubricating her anal opening with the slippery goo.
“Please! Please! Howard!” she wept. “It’ll hurt too much! I know it will! Please, honey! Let me take it in my mouth instead! Please, I’d like to do that!”
Howard stood directly behind her, and used his thumbs to spread her bottom cheeks apart as much as possible. Connie winced as his hands came in contact with her burning bottom.
“Now, hold still!” he instructed.
Limp with fright, Connie sagged against the top of the desk with her plump gluteal charms helplessly vulnerable. Howard stepped closer to her, allowing his throbbing penis to slip between the crevice of her buttocks and into the large dab of vaseline surrounding her pink anus. As she felt the sturdy masculine member probing closer to her small opening, Connie cringed with fear and sobbed heavily. Slowly, Howard allowed the tip of his penis to explore the entrance into the narrow channel.
“Oh, no!” Connie sobbed. “It’s too big! It’ll hurt something awful!”
Grasping the pretty blonde firmly at the waist with both hands, Howard began inserting his hard penis into the small aperture.
“OWWWWWWWWW!” Connie screamed as the crown-shaped head of his shaft began penetrating her anal canal, stretching the muscles wide apart. “FOR GOD’S SAKES, DON’T!”
As the head of his member disappeared inside the small opening, Howard paused for a minute and then began working it deep inside her. Connie wept as she felt herself impaled on the husky male weapon, and her sphincter muscles worked desperately in a futile effort to expel the foreign member.
“Please, you’re tearing me apart!” Connie cried, unavoidably squirming around before him.
After pausing for a moment, Howard slowly began moving his stiff member back along the warm, tight canal. As he did so, he slipped his hands down between her legs and began to fondle her charms. Connie reacted with a gush of girlish moisture, and wriggled her red posterior as he worked an exploratory finger between the outer lips of her vulva. As he continued thrusting his member back and forth deep inside the narrow channel, he worked his fingers deep into her hot and sticky pussy.
“Oooh! Ouch! Oh, my! Ow!” Connie reacted with a combination of pain and pleasure, pumping her rosy hips a little breathlessly.
As his manual caresses aroused her more and more, Connie began to move her hips back and forth with short, quick movements. His pulsating shaft slid easily back and forth within her anal canal, and he could feel her warm muscles clutching him tightly. Sliding a couple of fingers into her vagina, Howard pumped all the harder. Finally, he shoved his aching member as far into the small channel as it would go and spent himself with frantic spurts.
“Oh! Oh! Oooh!” Connie wriggled around breathlessly and suddenly climaxed warmly on his hand.
“You had better go get into that uniform now!” he told her when they had caught their breath.
“Please, do I have to?” Connie asked girlishly, rubbing her bottom gingerly.
“Definitely,” he told her. “Go see Gloria about borrowing some things from her.”
As it turned out, Gloria was waiting in her bedroom for Connie’s arrival. “I’ve got some things laid out there on the bed that will probably do!” the pretty teenager told her. “And let’s see, what else can I tell you? Oh, yes, don’t forget to remove your bra!
Blushing warmly, Connie began changing into the costume while Gloria watched with great interest, trying to conceal her amusement and succeeding only in part.
It was a half hour before Connie could bring herself to return to the study wearing a punishment costume almost identical with that worn by Gloria. As she blushingly made her entrance, Connie haplessly tugged at the abbreviated red skirt that failed to conceal her stocking tops and bare thighs, and was self-consciously aware of the outline of her full breasts pressing against the front of her thin blouse. To top it off, she wore a large red hairbow that made her feel completely juvenile. Connie’s pretty knees sagged slightly as Howard looked up from his desk with an admiring glance.
“Please, do I really have to parade around like this?” she pleaded with a scarlet face.
“I think you know the answer to that!” he told her quietly.