Ted sat up in the double bed, sipping an electrolyte drink, surprised at how much better he felt. The last attack, over an hour before, had been much less severe. By now, he was feeling back to normal. The program on TV bored him, so he turned it off. He showered and looked at himself in the mirror, shaved, and combed his black hair. Pulling on a pair of pants, he walked to the kitchen and made some toast.
At the kitchen table, he saw mail stacked to one side. Evidently Amanda, his girlfriend, had checked the mail before leaving for work. One item caught his eye, a magazine that discussed many sexual diversions, with reader’s letters given a prominent place. He smiled. In the three weeks they’d lived together, he hadn’t realized she subscribed to such a sexy journal.
This will be more fun than TV, he thought, taking the magazine back to bed.
Soon, he stroked himself and read of impromptu couplings, threesomes, semi-public sex, and the like. Then he came across one fateful letter.
I’ve enjoyed crossdressing since late high school. Like most CDers, I’ve felt guilty and purged my collections of frillies, but kept returning to the pleasure of silken undies.
I still fondly remember my first time. On a warm fall day, a girl in my class carelessly let her legs part (or was it carelessly?), affording me a peek up her skirt to black panties trimmed with lace. She was one of the prettiest, most boy-crazy girls in the school, and I got an instant boner. Sadly, class ended soon and she walked out hand in hand with her boyfriend.
But I couldn’t get my mind off her panties and how silky smooth and sexy they looked as I walked home from school. My sister was away at college but a lot of her stuff was in her room. I decided to see what her panties were like. No one was home, so I went straight to her bureau. Jackpot! Briefs, hipsters, bikinis – she had a real collection. The closest she had to the pair I’d seen were light blue with white lace trim. They felt so nice on my hand, I just had to try them on. I stripped quickly and sat on Sis’s bed as I slowly drew the silky panties up my legs. I stood up and snugged the waistband over my stiffness. Wow, that felt so good! I especially recall the smoothness of the nylon on my cockhead and the tight feel of the waistband across the split in my behind. I touched my hardness inside the panties and immediately saw a bit of wetness spread where my tip was outlined. I started rubbing myself. Even though I knew I’d probably make a mess, I couldn’t help myself….
Ted threw aside the covers and dashed around the bed to Amanda’s bureau. Opening one of her top drawers, he grabbed a pair of panties and sniffed the crotch hopefully. Clean. Dropping the dainty garment on the floor, he pawed through the bras, panties, and garter belts, some of which fell to the floor in his haste to find his favorites, a skimpy pair of pastel yellow with lace white lace panels on the hips. Already naked and rampant, he slid them up his legs and let the waist snap around his hips. “Ahhhh!” he gasped, like a long-lost traveler returning home.
Like the guy in the letter, Ted had loved playing in girls’ panties. He’d stolen some from clotheslines, but didn’t like doing that (plus he didn’t want to get caught). Eventually, he worked up his nerve and bought panties, pantyhose, even a garter belt and nylons, which he cherished despite the poor fit. Just before leaving for college, Ted reluctantly threw away all his pretty undies and he’d never lived with a woman since until he moved in with Amanda a few weeks before, so he’d not worn any. Up until reading the letter, he’d denied how tempted he was by the proximity of Amanda’s lovely undies.
But he couldn’t deny it now — gasping as he stroked himself, reveling in the forbidden pleasure so long denied.
*******
At work, Amanda realized she’d left some papers at home. She smiled. I’ll surprise Ted and see if he’s better, she thought. As she drove, she reflected on Ted. They’d known each other only three months, but he’d moved into her house three weeks before. He was usually attentive to her and made her feel special, but there were times he was thoughtless. Their free and open talks, their similar interests, and their sex…well, Ted took more time than most guys she’d been with to make sure she had a good time, so it was all good (except for the thoughtlessness). He kept telling her how beautiful she was with her long blonde hair, swelling bust and strong thighs. Amanda knew she wasn’t fashionably thin, but voluptuous. It was nice to be appreciated for what she was. On the way home, she bought him some hot and sour soup at a Thai place in the neighborhood. Once in the house, she put the soup on the kitchen counter before going upstairs.
She entered the bedroom just in time to see Ted, standing in her expensive panties, hips thrusting, hand rubbing, grunting, shooting white gobs of jism right through the panties to drip on the rug.
“What are you doing?” she gasped. She strode into the room, eyes snapping. The look of shocked surprise and shame on her boyfriend’s face left her unmoved. Then she saw her lingerie scattered on the floor. “Sneaking into my stuff and wearing my best panties! Cumming in them!…”
“I’m sorry,” Ted interrupted.
“Be quiet!” thundered Amanda, getting angrier and angrier. She noticed a wet stain on a pair of panties and a garter belt on the floor. “You wretch! You even sprayed on the clothes you threw on the floor! Take off those panties.” Trembling, Ted quickly obeyed. “Hold them up so I can see them. Stretch the waist. Yes, just as I thought. You ripped the waistband with your fat male ass. What else have you done?” She scanned the room, noting the magazine on the bed.
“N…n…nothing, Amanda.” Ted was terrified. He’d never seen his girlfriend like this, not even the time he’d been late and she spanked him. Would she break up with him? Spread his secret around?
Amanda took a deep breath. “Well, you’ve been naughty, far naughtier than simply being late for a date. What happened to you the last time you were naughty?”
“I got spanked.”
“Right. Well, this time, it’s going to be worse. Hand me the phone.” Ted hastened to obey. Though the phone was in Amanda’s reach, he wasn’t about to argue. With a swift hand, she took the phone and angrily punched keys. “Arthur? Listen, something’s come up and I won’t be back for the rest of the day. Can you handle the database requirement meeting at 3:00? Good. Thanks, see you tomorrow.” She held out the phone to Ted, who replaced it.
“Now, panty girl, what do you think are the reasons you’re to be spanked?” Ted stared at the floor. “Look at me.”
Ted looked into Amanda’s angry eyes and seemed to shrink. “For w…wearing your panties and c..cumming in them?”
“Yes, and?”
“Ripping the waistband and ruining your pretty panties.”
Amanda’s voice rose. “Yes, and?”
“Cumming on the other clothes and the rug…and scattering your clothes on the floor.”
With a snort, Amanda said, “All you can think about is my lingerie and your cum.” With a very sharp edge to her voice, she said, “What about invading my privacy, sneaking into my lingerie drawer? Isn’t that just a tiny bit naughty?”
“Yes, Amanda, it’s very naughty.”
“Then you agree you deserve to be spanked.”
“Oh, yes, Amanda, I do.”
“Good. Put the panties you ruined back on. I want you to remember why you’re being punished.”
As he stepped back into the lovely panties, he felt a bit of the thrill he’d experienced such a short time ago. When he snugged the panties on his hips, he erected immediately. An amused smile played across Amanda’s face. “I see,” was her only comment. “Next, pick up the lingerie on the floor. Separate the ones you soiled from the clean ones and put the clean ones back in the drawer.” When he finished, she commanded him to go downstairs and bring up one of the dining room chairs.
Ted reached for a pair of pants, but Amanda was having none of that. “No, naughty boy, go down just as you are.”
“B…but Amanda, someone might see me through the window.”
“Oh, well.”
Blushing, Ted scurried downstairs, quickly returning with a straight-backed, wooden chair. Amanda indicated he should place it between her bureau and bedside table.
Finally, Amanda sent Ted to the office in the spare bedroom to fetch an 18 inch, flexible plastic ruler. When he handed it to her, she placed it on her bedside table next to her hairbrush. She noted that Ted remained erect throughout all these preparations. She sat down, the lacy tops of her black stay-ups visible below the hem of her short skirt. She pointed to her lap and Ted, trembling, lay across her thighs, his panty-clad erection rubbing against her legs.
Amanda breathed deeply and rubbed her boyfriend’s bottom.
Ted, staring at the floor, frightened at the heat of Amanda’s anger and of the pain he knew he’d receive, nevertheless felt very aroused. As Amanda rubbed him, he recalled how some parts of his only previous spanking had been enjoyable and arousing. In the last few seconds before the blows began, he realized he wanted the spanking from Amanda, that it was right, that it was good for him.
For her part, Amanda was also aroused. The prospect of hurting Ted quite a bit, of having him submit to her power, went right to her head. With a smile, she commenced spanking her boyfriend.
She smacked his bottom, steadily increasing the force of her blows, maintaining a steady rhythm. Ted lay unresisting, accepting the punishment. After a bit, Amanda began lecturing, punctuating her speech with extra hard slaps. “In my sorority, we had a paddle that wasn’t just used for initiation. One of the most common spanking offenses was wearing another girl’s clothes without permission. But none of us ever, ever, EVER.”
“OW!”
‘…sneaked into another girl’s drawers! Take that and that and that!” Amanda slapped hard and fast as Ted grunted, gasped, and wrung his hands.
After a while, Amanda’s hand hurt. She stopped and inspected the results. Ted’s bottom, where it escaped from the tightly stretched panties, was red. She pinched it hard, digging in her nails. Ted gasped. “Your red bum looks very nice next to the yellow panties, Teddy.” She picked up the ruler and gave her boyfriend a few preliminary smacks with it. “How does that feel?”
“It stings, Amanda.”
“Good.” She applied the Plexiglas harder, taking advantage of its flex to increase the force on Ted’s inflamed cheeks. Some strikes now hit the tops of his thighs, for the punished boy twisted a bit. Amanda noted that the welts from the ruler were more sharply defined than the diffuse rosiness from her hand. Curious to see more, she paused. “Raise your hips, Teddy.” Ted obeyed instantly. Amanda slipped the panties down to just above his knees. “Oh, yes.” she said, “Your bum shows the ruler marks very nicely. It’s very pretty. And you’re still enjoying yourself, aren’t you, Teddy?”
“What do you mean, Amanda?”
“You’re all stiff.” She reached between his legs and gave his penis a hard squeeze and a wrench, quite unlike the caresses she’d bestowed on it when they enjoyed each other in bed.
“Unhhhh!” grunted Ted.
“What do you have to say for yourself, young man? Is this fun or a punishment?”
“It hurts, Amanda, and I don’t like that.
Smacking him with the ruler again, Amanda digested this information. Teddy just agreed to accept whatever she gave him and told her he found humiliation exciting. Nice! Smiling, she wielded the ruler fast, striking him with the tip all over his bum and upper thighs. She noticed he twitched and grunted or gasped when she struck the lower curve where his butt met his thighs. She concentrated on this sensitive area, and was delighted to see her boyfriend pound his fists on the floor. “Does it hurt more when I hit you there?” she asked.
“Oh, yes, Amanda, it sure does!” He spoke rapidly, his voice higher pitched than normal.
“Good,” she said, slapping harder. “Maybe you’ll learn to stay away from my things without permission.”
“I’m sure I will, Amanda. Ow, it hurts. I’m sure I learned my lesson.”
“Perhaps, but I want to make sure. Besides, I can do this as long and as hard as I want, can’t I?”
“Yes, Amanda, of course you can.”
After another over-all flurry with the ruler, Amanda decided to move to the main event, the hairbrush. She placed her hand on his bum and felt a bit of warmth. Her sorority experiences taught her the paddle would raise much more heat in Teddy’s bum. She grasped his penis, finding it still partly erect. She stroked it and evoked an immediate response, growth in length, girth, and stiffness. She pumped him twice, then twisted him painfully.
“Ahhhh!” Teddy cried. Amanda smiled. This is fun, she thought as she picked up her hairbrush. It had a rather long handle and a wide, flat back.
“Teddy, I want you to feel how warm your own buns are right now,” she told him.
Ted rubbed himself. “It’s warm, and it sure stung when you used the ruler, Amanda. Are you done? I’m sure I learned my lesson.”
Amanda laughed aloud. “Of course I’m not done, silly. I’m going to hairbrush you, and that will hurt more than anything I’ve done so far.” With that, she began smacking him with the hairbrush, lightly at first.
“Teddy, do you remember why you’re being punished?”
“Yes, Amanda, for wearing panties.”
WHAP! “No! Why?
“Owww!” Teddy gave the strongest squirm yet and his feet came off the floor. “For ripping the waist!”
Whap. “That’s one reason, not the main one. It’s very hard for you to learn, so I think you’ll be here a long time, Teddy.” Whap.
“For going into your stuff without permission.”
Whap. “That’s right, that’s the main reason. What are the others?” Whap.
Teddy, his bum noticeably redder than before Amanda used the hairbrush, jerked his whole body, but settled back into position. “Scattering your clothes on the floor.”
Whap. “Yes. And?” Whap.
“Cumming on them and the floor.”
Whap. “That’s right. What else?” Whap.
Tremulously, Ted said, “Amanda, I truly don’t remember any more.”
Whap. “Well, the hairbrush sure seems to have made you remember better. Say them again, in order of severity, starting with the most important.” Amanda wielded the hairbrush faster and harder.
“Owwww! Going into your things without permission. Ow. Ripping your panties. Ow. Scattering your (Ow.) things on the floor. OW! Cumming on them and the rug! Oh, please, Amanda, it hurts so much! Please.”
A big grin split Amanda’s face and she felt dampness between her legs. She loved hearing her boyfriend beg. So she continued to strike his bare bottom, now quite inflamed. Teddy was moaning continually, saying, “Please, Amanda, it hurts. Please!”
A thought occurred to Amanda. She slowed the pace and reduce the speed of her blows. “Teddy, tell me the truth. Was that the first time you wore my panties or did anything like that?”
“Yes, Amanda, I swear it.”
Amanda rained blows on his upturned bottom. Teddy kicked his legs and waved his arms, looking like a bird. “AAAAHHHH,” he cried.
“I don’t believe you, Teddy.”
“Ahhh. It’s true, I swear! The magazine…Ow! Please let me explain, Amanda.”
He sounded so desperate that Amanda thought there might be something to his story. Again, she lessened the blows.
“Oh, thank you,” gasped the punished boyfriend. “I used to love wearing girls’ clothes when I was a kid, but I stopped in college. Then when I moved in with you, the desire came on so strong, but I never did it until I read a letter about a guy just like me and how much he loved wearing panties. I couldn’t help myself.”
Whap. “Will you show me this letter afterwards?” Whap!
“Ow. Yes, Amanda.”
Whap. “Then I believe you.” Whap. “I’m going to hit you hard and fast, and while I do, you’re going to tell me the reasons you’re being punished, in order.” Immediately, she put her all into the hairbrush. It rose and fell steadily, striking right at Teddy’s most sensitive spots. The bird flapped his wings again in an instant. “AAAHHH! Going in your stuff without permission! OOOOO. Ripping your panties. Yahhhh! Throwing your stuff on the floor. Ahh…” Teddy was sobbing now, close to tears. “Cumming all over the place.”
“How do you feel about it now, Teddy?”
I’m sorry, Amanda, so sorry,” Teddy sobbed. One of the wings rubbed the bird’s face.
Amanda was thrilled. She’d made him cry. Oh, this is great. I love spanking Teddy, she thought. Still the hairbrush rose and fell.
“Please, Amanda, please stop. It hurts so much, I’ve learned my lesson. I’ll never do it again, but please stop! Amanda, please.” At that point, Teddy broke down completely and sobbed without reserve. After several more hard ones, Amanda put down the hairbrush and put her hand on Teddy’s bare, red cheek. It was hot! She reveled in the heat a few moments, listening to Teddy’s sobs and gasps. After a few moments, he sniffled, then sobbed a bit more, but more softly.
“Teddy, I’m proud of you. You took your punishment very well, and I’m sure you learned your lesson. Now, reach back and feel your hot ass.”
“Oh, wow, is that hot! You really blistered me, Amanda. I’m burning up!
“I like how red it looks. It’s very, very pretty, Teddy.” She leaned over next to his face and kissed a tear on his cheek. “I’m very pleased you cried, Teddy,” she said tenderly, her hand wandering between his legs. She realized when she touched him he’d remained at least partly erect throughout the ordeal. Again he stiffened immediately at her touch. For a few moments the two lovers rubbed, he his freshly warmed buns to get relief, she his member to prepare him for his next task. He twisted his neck and they kissed.
“Thank you, Amanda, I needed the lesson.”
Amanda gave a deep, contented sigh. To be thanked for giving him that….Wow! she thought. Then she felt a deep need for relief. She noticed Teddy had kicked off the panties with his thrashing. “Teddy, pick up the panties you ruined and put them back on.”
Still sniffling a bit, Teddy obeyed. “You look cute in them. I like the way your cockhead peers over the top. Now lie on your back on the bed.” As Teddy complied, Amanda reached up under her skirt and slipped out of her panties. “Now pull the waistband down below your ball-sack so your cock is ready me.” Teddy, smiling now, eagerly complied. Amanda straddled him and teased his cockhead for a moment. “Now don’t you dare cum before I do if you know what’s good for you,” Amanda said, dropping down on him. She gave herself over to her urgent desire and rode him hard and fast, slamming down to stimulate her clitoris. Teddy thrust up to meet her. Their loud breath turned to gasps. The pressure in Amanda built up and up, finally peaking. She screamed as she pounded up and down on her punished boyfriend, spasm after spasm coursing through her body. The cum lasted a long time as she kept riding Teddy.
Teddy gazed wide-eyed at his beautiful girlfriend as she came so hard. He gritted his teeth to prevent his own orgasm, wanting nothing more than to please her.
When Amanda opened her eyes, she saw the look of mingled awe and devotion on Teddy’s face and asked, “Are you ready?” He nodded. “Then let’s cum together!” Again she sped up. The two lovers gazed at each other. Teddy arched his back, pushing himself as deep into Amanda as he could and they both came, gasping, moaning, thrashing about, finally subsiding. Amanda lay down, cradling Teddy’s head to her breast.
The two lay like that for some time, then cuddled and kissed. “Show me the magazine,” said Amanda. Teddy fished it up from the floor where it fell during their frenzy. She read the letter while he watched her. Would she think he was creepy or queer?
When she was done, she regarded him with a quizzical smile. “So you liked wearing girls’ undies. How did you start?”
Teddy explained that his family visited another family, including a gorgeous 20 year old redhead, when he was 17. Fascinated with the unreachable beauty, he’d tried unsuccessfully to peep at her, but one day found her discarded panties and bras in the hamper. He tried them on and was hooked. He’d stolen a few pair when visiting friends, but that wasn’t good enough. He’d bought a few items, which made him extremely nervous, but threw his secret stash away when he went to college.
“Well, I think you look cute in panties, but mine are too small. You’ll have to replace my pair, and when you do, we’ll just buy you some — and other things, too.
“You mean I can wear panties? It’s OK?”
“Of course. But let’s talk about something else.
“OK,” said Teddy. He shook his head disbelievingly. He didn’t have to hide his desire any more. That was an overwhelming relief to him.
“Teddy, remember what happened after I spanked you that time you were late?”
He grinned. “Yes, we made fantastic love, but not quite as wild as just now.”
“So if I spank you, we have hot sex. I should spank you more often.”
“Not so hard as today! That really hurt.”
“Well, you were very naughty and I was very angry. Don’t you agree you deserved it?”
“Yes, and I thanked you for it and I meant it, even though it hurt so much.
“Well, you’ve never been late since the first spanking, have you?”
“No.”
“To avoid a spanking?”
“Not exactly, it’s more because you were right, it was rude and inconsiderate to be late and not call. I don’t want to worry you or make you angry. I love you, Amanda.”
“I love you, Teddy.” They kissed. Amanda kept it short.
“Do you think you’ll ever go in my stuff without asking permission again?”
“No way!”
“So Teddy, a spanking makes you more considerate and we have great sex afterwards. What about other ways you’re inconsiderate like leaving your things around, dirty dishes in the sink, not finishing projects, not putting your clothes away, stuff like that? Do you think spanking might help you in those areas also?”
“I dunno, maybe.”
“Let’s try it. I’ll spank you whenever I feel you need it and we’ll make hot love afterwards.”
“Well, OK, but I hope not so hard.”
“Oh, and one other thing. We’ll go get you some lingerie of your own, but for now I only want you to wear them when I’m getting ready to spank you. OK?”
Teddy looked down, crestfallen. He hoped to wear pretty undies when alone, like he did as a boy. But after a moment, he looked up to Amanda’s deep blue eyes and said, “Yes, Amanda, whatever you say.”
