Sissy Punishment Stories

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Sissy Punishment Stories
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Do sissies get spanked? They most certainly do. Not necessarily for being naughty, wicked or evil. Often for merely being sissies.
"Honestly, Maria, you look absolutely entrancing in that get up," Brandy Strong said to the woman reclining on the couch with her booted legs crossed, puffing on a cigarette through one of those long, slim holders. "Well thank you," the latter replied, dismissing the intended compliment with an air of indifference, as if she half-expected such comment. "Really, I harness myself in this attire because I find it comfortable, and it helps me assert my cast iron personality. At the same time its unconventional ... and you must know that I'm a non-conformist."
"I've known it a long time," Louise Kane the third member of the group interjected, as she reached toward the cocktail table for a cigarette.
Maria Hand, a jaunty dazzling figure, resplendent in her singular trappings, rose from the couch and walked toward the heavily draped window. She frowned pensively, wrinkling her ordinarily unfurrowed brow, as she smacked the whip she carried into the palm of her left hand.
"At any rate, girls," she said, "we're not going to turn our weekly visit into a critique on my wardrobe ... are we my dears?"
"Of course not," Brandy and Louise rejoined almost in unison, as their eyes met, then
followed with a knowing wink, as if both were partners to some deep dark secret. Brandy Strong and Louise Kane had dropped in on their quaint friend for what had become almost a weekly social. They engaged in bits of gossip and sundry chitchat, sipped her brandy, and spent what they often referred to, as an exciting afternoon.
They liked Marla, admired her bizarre habiliment that somehow seemed theatrical, and in a way envied her. They accepted her eccentricities, but were also conscious of the strong, domineering woman with the powerful, amazon-like chassis underneath the tailoring she affected.
Marla's uniform of the moment was indeed unique. It caused wonder and amazement to the two sidekicks. It also caused them to gape. For besides being merely outré, it had a frightening if not wholly menacing effect. She wore a brief, taut mantlet of glossy midnight black, that extended from the top of her hips to the line of her well developed breasts, enclosing them snugly and creating two mounds of unbelievable symmetry and blooming splendor. Made of supple black leather, the mantlet, more like a corset than a jacket, created a bulge that could be awesome to some guileless swain, if not outright devastating.
And the boots, well ... they were an inspiration, a figment of the imagination of some genius of the cobbler's craft. Long and tapering, they extended to about an inch and one half above the knee, lending emphasis to the whiteness of firm yet lithesome thighs. But what, more than anything else, staggered belief were the extravagant high heels with gilded spurs attached. Baroque and preposterous as they seemed, Marla nevertheless walked majestically, resolutely gripping a riding whip, not a trace of awkwardness in her stride.
Strangely enough a harmonious ensemble of sorts was achieved, and to crown it all was her head of hair, gleaming like polished ebony, flowing over her shoulders like strands of black silken threads that sparkled and glistened and blended agreeably with the short leather skirt, and the pliant fulgent gloves she wore up to her armpits.
"Y'know, Marla there's a story going around that your son, Sydney was the recipient of some extraordinary disciplinary treatment," Louise Kane turned her eyes toward Brandy's as she said this. Again that knowing look.., between them.
"Do you want to tell us about it, or am I stepping on dangerous ground?" she continued.
Maria laughed, but a faint suggestion of cruelty, barely detectable, twisted her lips for a brief moment. She smacked her left hand hard with the whip, then slowly turned to face the other two women.
"Dangerous ground my eye," she said to them, managing to control the tremors in her voice. "I have nothing to hide from you two ... or for that matter from anyone else in this town. If you're really interested and have the patience to listen I'll be glad to tell you all about it ... well?" "Oh, please do," pleaded Louise Kane, "Yes ... yes ..." echoed Brandy Strong.
"Very well then," Marla said as she strode over to the couch, tossing the whip on the table, then sitting down and crossing her booted legs.
"It all began about five or six weeks ago, I don't exactly remember the date, but I do know it was on a Friday. My husband, Justin, had taken me out to dinner and we returned home rather early ... I would say about seven thirty. He went up to the bedroom to grab a few winks while I sauntered over to the den, intending to wade through the evening newspaper. As I neared the door, the sound of scuffling, accompanied by shrill laughter, struck my ears. I was more than curious now, and even more puzzled. I quickly flung the door open and the sight that met my
eyes nearly floored me." Mafia paused, seemingly to catch her breath, while the other two hung on rapaciously to her every word.
"W-w-what w-was it?" Brandy Strong stammered, finding the suspense almost unbearable.
"Well ... I hardly know how to describe it to you. When I entered the room I saw what I assumed were two very comely young chicks.
Almost immediately I recognized Amy Young, Bridget's seventeen year old daughter, whom you must admit is a beautiful young lass. The other, for a moment or two at least, seemed an utter stranger. When recognition finally dawned on me, I was more than merely nonplussed, I was downright mad as all blazes ... yes, I admit... I saw red! For this bonny little miss underneath the frippery of powder and rouge was of all people.., my own son, Sydney!!"
When the immediate shock of Marla Hand's revelation wore off and a deathly silence settled over the living room, Marla slowly got up from the couch and suggested brandies and soda.
After pouring the drinks for the three, she returned to the couch. Sipping her drink passively she studied the countenances of the other two women attentively and began again.
"You both look very much surprised," she stated quite blandly, "but when you hear what I learned from Sydney, you'll be more than astounded ... you'll be flabbergasted! "As you know ... I may digress for a moment, I've been a member of The Lyceum of Strict Disciplinarians. And as you also must know, we are fervent advocates of bringing back the strap into our homes and penal institutions. In other words we believe that a good sound old fashioned spanking for spoiled brats and other incorrigibles, is a noble method for inspiring proper behaviour, and correcting minor faults.
The old saw, 'Spare the rod and spoil the child', holds just as good today, as it did yesterday. "Well, to get back to Sydney ... As I said before, my anger knew no bounds when I realized that this gorgeous bit of femininity was my own son. Yet somehow I managed a measure of self-control, though I couldn't quite keep the menace out of my voice when I harshly asked, 'What is the meaning of this, Sydney?' 'P-please t-try to understand, mother,' he whined, as the tears began to melt, 'these clothes are all a gift from Amy ... I have many more in my bedroom closet ... also ... they are gifts from her ... she's been most generous.'
"I was perplexed. I turned querulously to Amy Young, seeking some sort of answer to all this. But she remained silent. However, I couldn't help but note the marked degree of sympathy she displayed for my son. I was at my wits' end. I didn't seem to know for sure, how to cope with the situation. I was strongly tempted, there and then, to grab Sydney by the ear, march him across the room to the straight backed chair, and put him across my knees and smack his seat for all it was worth. Nevertheless I felt he was entitled to a chance to explain ... well ... I was prepared to listen.
'Y'see, mother,' he began, as he wiped his eyes with a lacy glove that he wore, and tried to compose himself, 'I've been terribly lonely. I have no friends in this town, other than Amy ... and ... er ... some of her friends are also mine. I never cared much for athletic games ... baseball ... or football ... I always found them much too rough ... even coarse. I do enjoy housework ... but you never allow me. I also love impersonating females ... Amy and her friends say I'm quite good ... as good or better than the many we've watched in the theaters and nightclubs in town.
'Y'know why I think I'm so proficient at it? I guess it's because I love the feel of silks and satins ... and ... this may bewilder you, mother, but I never could quite overcome my unquenchable longing to wear dresses and high heeled shoes. I do genuinely feel much happier wearing feminine clothing than I do male apparel. Don't ask me to explain why ... I simply don't know.
'Amy has been kind enough to present me with very attractive lingerie, which I frequently put on, four lovely dresses, and a smart little fur jacket which I simply adore. I hope that when I'm able to get a job, doing housework, I'll be able to afford an evening gown which I saw in Hobson's window, which I would like very much to have. I would feel very happy to be able to wear lovely clothes all the time, but up till now, the best I could do is to wear them in secret, here in my room.
'As you can plainly see, mother, this is a lovely sheath dress I'm wearing, the black fur trim goes all around the edge of the bracelet length sleeves. A black bra, panties, nylons and high-heeled shoes are all part of the ensemble, and notice my blue nail polish and eye shadow to match. My hair I suppose looks simply like a boy's bob. But I also have a small feather hat that harmonizes beautifully with the whole outfit. 'I really feel better and am more relaxed when I'm dressed in ladies' clothing, as I feel I am dressed as I should be.
'Two weeks ago I went out in this outfit, I had no lipstick and had to go shopping for some.
I went to several places before I could find the shade I wanted. The lady from whom I finally purchased it thought I was a woman until I addressed her.
'I said that I would like a certain lipstick. She very graciously got it for me, and was kind enough to hold up a mirror for me, as I applied it to my lips. She complimented me by saying I looked very nice, and that she liked the dress I was wearing. She said it was very pretty.
'What do you think, mother? ... is it very pretty?'
"Well, my dears, that did it. I could no longer contain my bitter wrath, I was all fire and fury, ready to explode. That last query of his, triggered all that followed, I'm now quite certain.
"'Is it very pretty,' I mimicked him mockingly ... I could not hide the utter contempt I felt ... I grabbed him by the arm with a high hand, and as I paraded him across the room I blared at him, 'You miserable popinjay ... is that the way I raised youP ... I'll teach you to garb yourself in women's clothes ...' and I unceremoniously pulled him across my lap after seating myself comfortably in the chair. Luckily for him, there was no hairbrush or a ruler available ... but I still had a good right arm. I pulled up the dress he had no right to masquerade in, and I let him have it. 'This will teach you the right lesson,' I remarked ominously, as I smacked him where I thought it would do the most good.
'P--please m--mother, t--try to u-understand, p--please ...' he whimpered ... but I was merciless.
"I realized almost immediately afterward, that I hadn't acted entirely correctly myself. You see, being a member of The Lyceum of Strict Disciplinarians, I should have known better than to have spanked him in the presence of Amy. It is too humiliating for a young man to have another person, especially one of his own age, to witness his plight and, to top it all, a member of the opposite sex.
"By the time I exacted a promise from Sydney that he would never again behave like a sissy, nor dare to dress himself in feminine clothing, Amy Young, apparently feeling a deep empathy with Sydney, made a dash for the door. With a wailing lament escaping from her lips, and tears streaming down her cheeks, she abashedly made her departure."
Louise Kane quietly and unobtrusively got up from her chair and walked over to the cabinet that served as a bar. She was a pretty little woman, shy and rather demure. She poured herself a drink, took a small sip, and then almost stealthily tiptoed back to her chair. Now, sitting back contentedly, the glass of brandy in her hand, she felt the time had come for her to make her contribution to what up to now seemed just a dialogue between Maria Hand and Brandy Strong.
"Mafia," she began, "I never could understand your joining a group of what I consider cruel ill-disposed misfits, crackpots ... if you will pardon the expression ... I'm talking about that crowd who comprise the membership in that organization of yours, The Lyceum of Strict Disciplinarians.
"If that's where you get your ideas on how to handle a problem like your son, Sydney, then all your coaxing will never get me to join up. I know you mean well ... I've weighed all your arguments, and to be quite frank, there were moments when I began to see things your way, I was often tempted to become a member. I needed a little time ... but your manner of disciplining Sydney has destroyed any illusions I may have had. Imagine spanking a young man attired in feminine clothes ... and allowing a young lady like Amy to witness his humiliation.
I'm glad at least that you have the backbone to admit you were wrong.
"Granted that Sydney deserved punishment.
But I'm sure a better method ... perhaps less painful could have been used."
Louise Kane stopped to catch her breath.
The words had poured out unconsciously like an endless cascade. Now newly sprouting doubts began to assail her. She looked at Maria and Brandy. They remained silent. Louise took a deep breath and was about to continue, when Maria Hand interrupted.
"Okay then ... How would you have handled a similar situation?" the latter asked, not bothering to suppress the biting sarcasm in her voice.
"Well ... er ..." Louise hesitated, now not quite sure of herself. "I ... I would have petticoated him. That is, I would have dressed him in the kind of clothes he seemed to prefer ...just to show him how ridiculous his choice was.
I would let him wear panties, and say to him, "Well ... you think you'd like to be a girl, okay ... be a girl," I would then let him put on a bra, a frilly slip and some short frock, that would complete the transformation, then I would get rid of his masculine clothing. I would then jibe and sneer at him, and perhaps call in one of his girl friends and allow her to see him in his new petticoats and all. Word would soon get around, and before very long, his friends would call. He'd soon begin to hate his petticoats, when his friends commenced their laughter and their denunciation. I find it amusing to visualize him sitting with his knees together, trying desperately to hide from sight those frilly panties, of which by now, he is utterly ashamed.
That, my dear, Marla, is the way I would cope with a difficulty like the one you've had to face.
As for spanking him ... and in the presence of Amy Young ... well to me, that smacks of downright cruelty, and for the life of me, I could never sanction it."
"Poppycock," was all that Marla Hand could utter by way of comment upon Louise's excursus, as she reached over for a cigarette that lay in the miniature chest on the low table flanking the sofa.
"I think your attitude is all wrong, Marla ...there's a lot of sense in what Louise has to say," Brandy Strong obtruded at this point. "I don't exactly buy what Louise has to sell ... but, I do agree that placing Sydney over your knee and spanking his bottom in the presence of Amy ... must have been most humiliating ... on that score I admit I see eye to eye with her. What I disagree with and that most vigorously ... is the substitute method she advocates."
"Aw ... nuts!" was all that Marla could manage.
"Oh, yeah ..." this from Louise Kane, "You got any better suggestions?"
Not in the least perturbed by their denigrations, Brandy continued.
"To be perfectly frank, Marla," she said calmly enough, "and I know you're not going to like hearing this, but I'm firmly convinced that your son, Sydney, is a sick boy. As a matter of fact, I'm inclined to believe that all sissies are sick people. What I heartily recommend is that you don't raise his skirts and ... spank his posterior, nor permit any outsider to witness such an experience ... where a callow young man is permitted to suffer such an outrageous sense of shame.
"On the other hand, Marla Hand ... please forgive the pun... I exhort you to see a doctor ... a psyshiatrist ... now please, don't snicker ... I'm in deadly earnest. The boy needs help ... and as I see it, his is a mental problem ... not one that you or I can solve that easily."
Marla was filled with doubts and misgivings, and her reactions weren't as light as she made them appear when she lightly dismissed Brandy's counsel with a flippancy, "Aw, baloney."
On the other hand Louise reacted differently. Brandy's words seemed to have made a marked impression. For a moment or two she hesitated. Then, framing her sentence very carefully, she uttered quite simply, "Y'know there might be something in what Brandy says." At that point the doorbell rang ... loud and clear.
"That must be my husband, Justin," Maria said.
The girls didn't need to be hit over the head, they could take the hint. Without fuss or further ado, they quietly let themselves out through a rear exit, after bidding their gracious hostess an endearing 'au revoir'.
Sydney Hand was excited. In fact he was intensely elated, something wonderful had just happened. He had just finished talking with Amy Young, and, of all things, she had invited him to attend her sorority affair on the following Friday night. "Come as a girl," she had pleaded as if pleading was necessary. Without giving it a second thought he jumped at the opportunity, saying, "Certainly, I'll be delighted to attend ... will there be an initiation of sorts?" "By all means," came the reply.
Of course there was the matter of a promise Sydney had made to his mother ... and the dire consequences that could result from a failure to live up to it. "But," he assuaged his grating conscience, "she need never know ... for that matter no one other than Amy need know, and I certainly can trust Amy. Then again, one has to live dangerously every once in a while." A general air of excitement prevailed at the sorority house of Phi Alpha Epsilon on Friday mght of March third. Everyone seemed in a dither, especially Amy Young, who kept looking at her watch, then at the door. As the hour drew close to nine o'clock her impatience seemed on the verge of exploding. She got up from the bench and wormed her way through the milling throng of sorority sisters and their friends, till she reached the door that led to a balcony
overlooking the lane that led to the main entrance of the building. Failing to see what she so eagerly hoped for, she returned to the room and, after a bit of pushing and shoving, managed to get back to her seat. A look of utter disappointment appeared on her face. Then it happened.
Glancing up toward the door out of sheer inner necessity or compulsion, she espied that which had been the cause of her many anxious moments.
Striding through the entrance with a queenly grace and regal bearing was what at first seemed an appariti
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