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Amanda's Discovery, Part 2: Shopping

Teddy is humiliated and punished by his gf and strangers. He smiles when it's over.
Shopping

After his ordeal, Ted fell asleep for some time. A few moments after he awoke, he remembered the spanking and tentatively rubbed his behind. Cool, but tender. He noticed his cock and tucked it back in the panties. “Amanda?” he called.

“In the living room.”

“Just a sec.” Desperately thirsty, he took a big drink at the bathroom sink, then walked to the living room, wearing only the panties. Amanda, seated in an easy chair, smiled and held out her arm. They kissed, long and deeply.

“Amanda, I want to tell you how...um...humbled and honored I am that you accept my need to wear lingerie. It’s such a relief.”

“I’m sure it is, dear. And I’m glad you accept my discipline to help you be more considerate and thoughtful.”

Ted grinned. “I think it might do me good, but I know we’ll have fun.”

“I’m sure of it. I had a lot of fun after the initial surprise. I walked in to see your cum shooting through my panties!” They looked at each other, grinning, then started laughing. Once started, they went on and on. Soon both wiped tears from their eyes. As they slowly recovered, Amanda said, “You looked so shocked, surprised, embarrassed, afraid, all at once.”

“I was terrified, thought I’d lose you, Amanda, and I couldn’t bear that. I love you too much.”

“Not if you’re good, honey. Well, you slept a long time after your big spanking. It’s 4:30 and we’re going shopping tonight. How do you feel after your illness?”

“Much better. I ate some toast just before you came home, drank Gatorade.”

“Good. I thought you might be dehydrated. I checked on you a couple of times while you slept, but you seemed OK.

“Thanks, love.”

Amanda instructed Teddy to get dressed in slacks and a shirt with no undies and to make a simple diner.

“OK, Amanda.” Soon, he brought Amanda a salad, cheese and crackers, and white wine.

Amanda remained in the chair, but indicated Ted should kneel at the coffee table. As they dined, Amanda asked Ted about the lingerie he liked. He told her panties, stockings, and garter belts, even girdles turned him on but, pantyhose less so.

Their meal finished, Amanda told Ted to bring the panties with him and he put them in his pocket.

Amanda drove across town to a large strip mall next to a major shopping center and led Ted to Valerie’s Unmentionables, a lingerie specialty shop. Nightgowns and skimpy outfits draped mannequins, bras and panties hung from displays or filled bins. Some casual wear and slinky dresses were on display. Several mirrors lined the walls. The small register desk nestled to the right of the entrance. A short hall at the back led to dressing rooms and a full-length triple mirror.

To Ted’s surprise, Amanda hugged the proprietor, Valerie, a tall, slender brunette. She introduced them and Ted learned that the two ladies had been in sorority together.

“Ted and I have been living together for three weeks.”

“How nice,” replied Valerie. “You’re a lucky boy, Ted.”

“Amanda’s great. I’m so glad to be with her.”

“Val, remember how in the sorority sometimes we’d have trouble with girls borrowing stuff without permission?”

Valerie laughed. “Yeah, it was worth three swats with the paddle, I remember.”

“What about rummaging through a girl’s drawer to get stuff?”

“I don’t remember that happening. Sometimes girls would snag something left around or in the laundry.’

“Well, Ted needs to replace a pair of my expensive panties. Show him, dear.”

Embarrassed, Ted produced the damaged panties from his pocket. “Here.”

“Hold them up so she can see.”

Miserably, Ted held up the panties, spreading them with his hands. The other customers stopped shopping and glanced at him curiously.

“You bought these only a few weeks ago, Manda, now the waist’s ruined. What happened?”

“Tell her, Ted.”

“Must I?”

“Yes.”

“I...I ripped the waistband.”

“Tell Valerie the whole story, Ted, and what happened when I found you.”

By now, all three customers in the small boutique openly eavesdropped. Blushing, stammering, Ted recounted his uncontrollable urge to wear panties, the destruction of the sexy garment, his masturbation and the severe spanking. Amanda stopped him before he told of their frantic lovemaking that followed.

Amanda said, “So, Valerie, I don’t mind if he wears pretty things. I think it’s sweet, so I want him to replace my panties and buy...um...some outfits.”

The three customers crowded closer, nodding approval.

Valerie grinned. “Good idea, ‘Manda. Make your selections while I help these customers.”

Amanda and Ted walked to a rack where several panties hung from hangers. Ordered by Amanda, he rummaged in the displayed panties until he found the right size and model. They carried the panties back to the register and put them to one side. Amanda noticed a tape measure and discovered Ted’s waist was 34 inches.

“Valerie,” she called across the store. “Ted’s waist is 34 inches. What size panty should he wear?”

Valerie thought a moment, then said, “Well, men’s waists correspond to women’s hips, so medium.” By now, Valerie and all three women customers openly grinned and exchanged knowing looks.

One woman gave Amanda a big smile and approached her. “I’m Anna and I spank my husband, too,” she said. “It does wonders for our relationship and for his behavior.”

Amanda wanted to know more. “Just a moment, please,” she said. Turning to Ted, she said, “Go to the bin over there and select a pair of white briefs, medium. If you see others you like, you may take some, but be quick. Then go put the briefs on.”

Miserably, Ted said, “Yes, Amanda,” and trotted off.

Amanda spoke to the woman. “I’m Amanda. Today was only the second time I spanked him, and by far the hardest, but I loved it. And the aftermath! Wow!”

“I’m Anna. It is nice to get sexual relief after giving a spanking. But when my boy’s truly misbehaved, there’s lots of satisfaction afterwards, but it’s all oral and one-sided — mine. After punishment, it’s a long time before he gets any fun, not even masturbation. It keeps him docile and trying hard to please me, as you can imagine.”

With a glint in her eye, Amanda said, “But he’s so... vigorous after he’s been spanked.”

“Sure. So spank him when he hasn’t misbehaved, but not so hard, then fuck him. Sex after punishment gives a very mixed message to a boy. Sex after a foreplay spanking gives the message that you love spanking him and reward him for good behavior, punish and deny him sex for bad. Try it. You don’t know yet how far you can push him, but it’s so much fun.”

“Wow,” breathed Amanda. She saw that Teddy had selected a few panties. He stood hesitantly outside the short hallway that led to the changing rooms. Excusing herself from the woman, she went to Teddy.

Barely able to meet her eyes, he held out the briefs and mumbled, “Do I really have to try these on, Amanda?”

“Yes, Ted. We’ll buy them so you can wear them under the other things you try. I know wearing panties excites you, so if you have an accident in those, you won’t soil anything that belongs to Valerie.” The customers, still listening, suppressed laughter at this. Shoulders slumped, Ted went into the changing room. Amanda exchanged grins with the women, then followed Ted inside. He finished pulling the briefs up, a pretty pair with lace at the legs and appliqued flowers on the front. They covered him to the waist. As always, panties induced an erection. Amanda smiled, inspected the fit, and told Ted to put his pants back on and come out to shop.

Together, under the amused eyes of the women, they selected several bikini and hipster panties, garter belts and stockings. Valerie rang up two women’s purchases, but no one left the shop. A young woman in a miniskirt dropped a package. She twisted around and bent to retrieve it, her legs and part of her bottom in sheer tan pantyhose exposed. Teddy stared, transfixed. Amanda, Valerie and the other women saw and drew in sharp breaths of disapproval.

“Teddy, stop staring at that woman. She’s not putting on a show for you.”

“I’m sorry, Amanda, I couldn’t help myself.”

“Right, just like you couldn’t help yourself when you rummaged my undies drawer today.” The woman in the miniskirt, package in hand, glared. “You see,” Amanda continued, “she’s offended at your staring, right?”

“Yes, indeed. Staring at me right in front of you, his girlfriend. You ought to be ashamed of yourself, young man.”

“What do you have to say for yourself?” prompted Amanda.

“I’m sorry, Miss,” said Teddy.

The woman regarded Teddy with disdain and Amanda snorted. “That’s not enough. Back to the dressing room with you.” Head down, Teddy went into the dressing room. Amanda handed him a lacy, pale blue garter belt and he fastened it around his waist and rotated it into position.

“Tuck the garter belt into the panties.” Teddy obeyed instantly. Amanda opened a pack of long, tan stockings with black Cuban heels, seams, and welt.

Teddy, stiff with embarrassment but aroused by the feminine garments, gasped. “Oh, what beautiful stockings.” Sitting on the bench, he prepared a stocking and rolled it up his leg.

“Don’t forget to check the seam,” warned Amanda.

Teddy glanced up and saw the three customers and Valerie grinning at the door. “Ohhh,” he moaned, but didn’t object.

“See how much Teddy likes his panties? He’s all rampant and even stained his new undies.”

He glanced fearfully at Valerie, then Amanda. “I’m sorry, I can’t help myself.”

“I’m getting very tired of hearing that lousy, ineffectual excuse, Teddy. Get the other stocking on.”

As soon as Teddy attached all four garters, he stood for inspection. The women agreed he looked adorable in his frillies.

“But we still haven’t dealt with how lewdly you stared at this woman...”

“Cynthia.”

“...at Cynthia. Come out of there and bend over that fixture with all the panties. You like panties so much, well, you’ll see as many as you want while you take your spanking.” Amanda strode to the main part of the store, depositing the lingerie she intended Teddy to buy near a mannequin.

As Teddy complied, crossing the room to the panty bin, Valerie put up a closed sign, locked the door and pulled down the blinds.

“What do you have to say before I begin spanking you?”

“I’m sorry for staring at you, Cynthia.”

Anna spoke. “When I punish my husband, I always have him ask for punishment and thank me afterwards.

“Teddy?”

“Please spank me, Amanda, so I’ll learn self-control and not stare at women.”

“Certainly, since you ask me so nicely.” Amanda swatted Teddy’s bum as the spectators encouraged her. “Give it to him.” “Harder.” “That’s the way!” “Make him smart.” “Oh, that was a good one, Manda.” “What a zinger!”

When Teddy started twitching a bit from the sting, Amanda, with a conspiratorial grin to her new friends, tugged the white panties down, a telltale damp spot on the front.

The third customer, a well-dressed woman in her late thirties, bent down and peered between Teddy’s legs. “Oh, he’s not dangling. Must not hurt enough yet!” She giggled. “I don’t believe I said that, but this is fun.”

“Yes, it sure is,” grinned Amanda, striking with renewed force. “What do you think, is this fun, Teddy?”

“It’s really fun to wear the lingerie...OW! The spanking hurts but it’s good for me...Ow...so I don’t mind. OW! I’m truly glad to give you ladies pleasure. Ouch!”

“Good.”

Anna opened her voluminous purse and produced a small cat o’nine tails, deftly demonstrating how to swish it back and forth. She then handed it to Amanda with a smile.

Eyes glinting wickedly, without warning Amanda applied the cat rapidly back and forth across Teddy’s backside. The crossdressed man cried out and jumped up involuntarily, fearfully glancing back.

“Get back in position, you,” snarled Amanda, pushing his back. Gasping, Teddy replaced his hands against the bin and braced himself. The cat again swished its tail. Teddy began moaning, his feet bouncing off the floor.

The well-dressed woman said, “Oh, the spanking dance! I used to loved to see my brothers and cousins do that. It’s been years. I’m going to have to start spanking my boyfriend.”

All the women laughed.

Teddy was nearing his limit. Still dancing to the cat’s tail, voice shrill, he begged. “Please, Amanda, please. It hurts so much. I’m sorry I looked at you, Cynthia, and I’ll change my habits. Please, Amanda, I learned my lesson.”

“Are you crying yet, Teddy?”

“Yes, Amanda, yes, please!” He danced franticly now, his feet pumping up and down, bottom swaying a bit, but always presented for Amanda to administer punishment.

“Cynthia, Teddy’s crying and begging. Do you think that’s enough?”

“Maybe a little longer. I like seeing a man like this when he treated me lewdly.”

“I’m sorry, I forgot, you are the injured party here. Why don’t you show Teddy what you think of him, dear?” She offered Cynthia the cat.

“Oh, thank you! I think I’ll start with my hand.” Cynthia rested her palm on Teddy’s inflamed cheeks. “Oh, he’s warm.” She rubbed his bum, then began spanking. “Let this be a lesson to you, young man. Don’t you dare stare at me.”

“Yes, Miss Cynthia, I’m sure learning my lesson!” sniffed Teddy. After a few moments of hand spanking, Cynthia swung the cat and Teddy began crying and dancing again.

“Oh, this is such fun, and he so richly deserves it. Thank you, Amanda.” Cynthia got in a few more swats, then handed the cat back to Amanda.

Teddy hung his head, danced a few more steps, and sniffled back more tears.

Amanda regarded him for a moment, then, grinning, offered, “How about the rest of you? Why doesn’t everyone take a turn?”

Teddy moaned.

The well-dressed woman took a deep breath. “I think I’d like to. By the way, I’m Penelope,” she said, reaching for the whip. Taking her position behind Teddy, she also felt his red cheeks. “Oh, wow.” With that, she began spanking, tentatively at first, then much more briskly. Holding the cat’s woven leather handle between her teeth , she slapped him hard with both hands. “I had no idea this would be so exciting!”

“Oh, that hurts!” cried Teddy.

“It’s supposed to hurt, it’s a punishment,” put in Anna.

“Yes, that’s right,” emphasized Penelope, switching to the cat. Teddy just moaned and immediately renewed his dance. “Take that, and that, and that!” Penelope took wide swings with hard swats. Teddy, to no one’s surprise, cried anew.

Visibly taking control of herself, Penelope offered the cat o’nine tails to the others. Anna indicated that Valerie take the next turn. Again, Teddy got spanked, then whipped. “Manda, how many guys did we feel deserved to be swatted with the sorority paddle?”

“Way too many to count, hon.”

“That’s right, but now I’ll make up for it on Teddy!” Valerie spanked with the palm of her hand curved to fit Teddy’s hot, red bumcheeks, yielding a satisfying, loud smack each time. She, too, wanted to make him dance, so she switched to the cat.

“Oh, please, this hurts. I’ll never look at anyone but Amanda, please stop. It hurts so much already and there’s one more spanker to go!”

“Who will you look at, Teddy?”

“Amanda, only Amanda. I love her! Oh, this hurts, I learned my lesson!”

“I hope so, you silly boy.” Valerie gave a few more swats with the cat, then, clearly reluctant, yielded the instrument to Anna, who had extracted a foot long rattan from her bag.

With a confident smile and a wink to Amanda, Anna strode next to Teddy, bending down next to his ear. She spoke loudly enough so the others could hear, all the while scratching Teddy’s inflamed cheeks with her sharp fingernails. “Teddy, you’ve had the hardest and most embarrassing punishment of your life today.” Choking back tears, Teddy nodded. “These ladies have been very excited and gratified to spank you, and they’ve done a good job. However, I’m very experienced at punishing wayward boys, so you’re about to experience the most pain yet. I always give the boys I punish a way to demonstrate that they’ve learned their lesson. Listen carefully. I’m going to spank you in a new way, then use the cat, then a small cane I carry as well. This will hurt quite a bit, and you’ll show me you learned your lesson by not dancing. You are to keep your feet on the floor at all times until I tell you to dance. I will send the sharp leather tendrils of the cat across your bottom 20 times, then use the cane for the traditional six of the best. If you dance during the cat, I’ll start the 20 over. If you dance while I cane you, the six begin anew. Is this clear?

“Yes, Miss Anna,” Teddy choked out in a terrified whisper.

“Repeat the instructions.”

“No dancing for 20 cats and six canes.”

“That’s correct.” She placed both spanking implements in her mouth. Without warning, she thrashed the punished crossdresser’s bottom with the flat of her hand, hard and fast, then suddenly scratched his bum deeply, her crimson nails making white marks that contrasted with the red flesh, quickly reverting to red.

“AHHHH! cried Teddy, utterly surprised. His body curled forward in a vain attempt to avoid his punisher, but his feet remained on the floor. Amanda snatched the cat from her mouth, quickly turning it in a figure eight motion in the air, then moved to strike Teddy.

The whirling tendrils struck Teddy with a curling motion, faster and harder than any before. He cried out inarticulately, screaming the entire time Anna whipped him, but his feet didn’t move.

Twenty hard swishes took only a few seconds. Dropping the cat, Anna grabbed the cane and struck Teddy’s bottom sharply. “Yaaahhhh!” shrieked Teddy, but his feet remained on the floor.

Anna took few aiming taps, and kept the pace swift, allowing the hapless male little respite. Teddy shrieked aloud with each stroke, pounding the bin with his fists in an attempt to dissipate the sharp pain while remaining obedient.

For the last three strokes, Anna, clearly hoping Teddy would fail, moved back a bit and let the tip strike on the nearer cheek, using the full force of the flexible cane. Teddy, beyond crying, shrieked continually, yet his feet remained as though planted to the floor of Valerie’s boutique.

After the last stroke, Anna said, “Very good, Teddy. You may dance and rub your behind. Face away from us so we can watch. You see, girls, males can control themselves; they just need the proper motivation.”

All the women heaved deep sighs at the end of the spanking. Anna, Amanda, and Valerie were beaming. Amanda stretched her entire body like a cat in heat. Valerie hugged her body and surreptitiously cupped her breasts, clearly aroused. Cynthia smiled and shifted her weight from one leg to the other. Penelope stared, wide eyed and open-mouthed. She glanced at Anna and Amanda. “I always wanted to make a boy do the spanking dance. This was quite an experience.” She grinned like the others. “I do want to do it again.” She looked at Teddy, still hopping from foot to foot, his hands rubbing his red cheeks and upper thighs. “Look,” Penelope said, “that softened him up. He’s waving in the air, just like my brothers.”

“Keep dancing, but turn around so we can see, Teddy,” commanded Amanda.

Teddy obeyed, and the ladies pointed and laughed. “Look at it bob up and down.” “Isn’t that darling?” “It wags like a tail.” “Like a cat o’nine tails!” They all laughed at that. “Look,” said Valerie, “It likes this, it’s growing again.”

“Keep dancing, Teddy, and thank us,” said Amanda.

“I thank you all for spanking me. I learned my lesson and I won’t ever look at a woman that way. I love Amanda and she means everything to me.”

“Thank us all, and apologize again to Cynthia.”

Looking at each woman in turn, Tedd said, “Thank you, Penelope. Thank you, Cynthia, and I’m truly sorry I offended you by staring. Thank you, Valerie. Thank you, Anna, and most of all, thank you so much, Amanda.”

Amanda selected a pair of panties from those she’d put down earlier. “Teddy,” she said sharply, “stop dancing and put these panties on.” She handed him a pair matching the garter belt.

As Teddy slid the panties up his legs and over his hips and penis, his penis grew to its greatest size. “He’s adorable in those undies.” “Cute, very cute.” “I’m bringing my boyfriend here, Valerie.”

Anna added a critical comment. “You look lovely, Teddy, but the effect is marred by pubic hair. So many men like to see us hairless, they should be shorn as an indignity. It’s more boylike and more effeminate.”

“You’re just full of good ideas, Anna,” beamed Amanda. She looked at her boyfriend in the lacy undies and fancy stockings. “Gosh, I need relief. I’m horny.”

“Why don’t you take Teddy to the dressing room, Manda, while I ring up these nice ladies’ purchases?”

“Another great idea!” Amanda took Teddy by the hand and led him to a dressing room, closing the door.

The room provided visual privacy, but as Valerie completed the transactions, Amanda’s moans and groans, and a few more smacking sounds, came from the dressing room. All the ladies grinned. Valerie asked, “Anna, where did you get the whip and cane?”

“From this shop,” she said, passing out business cards and leaving an extra for Amanda. “I’m one of the owners.”

The women shared a few comments about how they intended to add spanking to their lifestyles, waiting for Amanda to finish using Teddy. After one last, loud peak, the envy of all the other women, Amanda, flushed and smiling, led Teddy out, pulling him by his still-erect penis. His mouth and chin were still wet. Valerie and her customers clapped and hooted. Amanda grinned and took a bow. Teddy managed a smile.

Amanda said, “Hi girls. I feel much better. I hope you get satisfied when you get home.”

Cynthia whispered, “Watch this,” to her new friends. “Teddy!” she called. When he looked at her, she lifted her miniskirt to her waist exposing shaven pubes in her pantyhose.

Teddy instantly twisted sideways to avoid the sexy, arousing sight. “I’m not looking!” he squeaked, clearly terrified the ordeal would begin again.

“Well, he passed the test. He clearly learned his lesson! Three cheers for us!” said Amanda.

“Hip, hip, hooray! Hip, hip, hooray! Hip, hip, hooray!” laughed all five women. A smiling Teddy joined in.

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