Sissy

Sissy

It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties.

Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many of his kind, had considered her up until this moment only as the beautiful, dutiful, and thoroughly reasonable woman she appeared to be. It was thus with a kind of paralysing incomprehension that he gauged her reaction.

She laughed.

Not unkindly; at least, not unduly so; and not out of embarrassment. In fact, there was something of the veteran's experience in her sneering guffaw, which appeared to him so utterly unaccountable. He didn't know what perturbed him the greater, being caught by his wife (and her friend!) in a pair of women's underwear, or this new woman suddenly emerged before him, his wife no less!

'Look, Miri. My husband's got my panties on!' Miriam looked on amused.

Brad froze on the bed, abruptly divested, expunged, evacuated of his usual air of self-possession and authority with such cruel suddenness that he almost burst into tears. She circled him like a lioness, a natural predator sniffing his palpable vulnerability. Her orange ruffle skirt bounced tantalisingly close, and the waft of the two women's expensive perfume invaded the stuffy loft bedroom, oppressing him powerfully as he tried desperately to shrink into himself on the bed covers, wishing to swallow up into a void.

Sandra exuded a mastery he had not before suspected her capable of. Her poise was coloured by an overt, aggressive, sexual attitude. She frolicked around the bed, at once deploying her resounding feminine charms, while at the same time intimidating in a quintessentially masculine fashion. Her friend was equally delighted in her display, and stood leaning in the doorway, as if minding the exit, with a mocking smile of feigned disbelief playing across her wide thin lips. They were like two bullies in an ally, down which a hapless young rich boy had happened to wonder.

Sandra came to a stand-still in front of him and tutted disparagingly. She leaned over with her hands on her hips, legs slightly apart and pushed her ripe cleavage forcefully towards his cringing form. One of the string straps of her black vest top had fallen jauntily off a shoulder and he couldn't help but marvel at the peach perfection of her ripe skin. 'Well, well, well.' She pondered aloud, 'What are we to do with little Bradly here?' She squealed lightly and then giggled, as if tickled by the novel image for the first time all over again. 'And he's chosen one of my softest cotton panties too!' She exclaimed, her voice morphing into the exaggerated coo of a mother coddling a baby. Miriam snorted loudly. 'Well, if he wants to dress up in my clothes, let's help him.' Sandra beamed decisively, as if suddenly enlightened by the best of all ideas. 'He'll need a skirt to go with those panties.' And she turned spritely to rummage in her wardrobe.

What was even more shocking for Brad was the total contradiction between Sandra's usual docility and her current masterly demeanour. Not that she was especially timid or quiet, indeed she was socially well adept, but she definitely didn't routinely impinge upon him with her own oppressive desire. She was rarely uncompromising or imposing. Sexually she was neither introvert nor extrovert; he thought they had a very healthy sex life, perhaps even somewhat dull in its normality. She wasn't a massive flirt or exhibitionist; though she was stunningly attractive, with a curvaceous figure and petite frame, generous, firm breasts, with fat nipples that stood out now through her finely-ribbed black cotton vest top. She owned a beautiful pair of deep, dark pink lips, the same colour as her aureoles, soft, creamy skin that turned a delicious peachy pink in the sun as it was now, and ripe, firm buttocks which she enjoyed to be spanked, particularly. But now, here in their own bedroom, with his face a bright scarlet and his limp dick cringing pathetically in a pair of her knickers, slightly damp from his sweat and the excitement he was enjoying before they had burst in upon him so unreadily, she seemed an altogether different animal: commanding, superior, a playful arrogance corrupting her usually sympathetic smile. And leering flagrantly at him from the doorway was her friend Miriam! There was no sympathy in the heavens today.

Sandra had come home with after bumping into her friend while out shopping. She'd invited Miriam to join her for a coffee, and as they'd lunched together over a large wine and small salad their conversation had turned toward the more bawdy of subject matters, as women of their kind are sometimes want to do -- 'women of leisure', as they say -- so Sandra had invited her friend back to her place for an afternoon Pimms and a spell in the garden; Bradley would be at the office she was assured. They'd just been making their way upstairs for Sandra to show Miriam the new outfit she was planning to wear, for Brad on a date they had coming up -- their six year anniversary, to be precise -- when they had been so surprised to find him in such compromising a position; Miriam, for one, had only known Brad to be a man entirely typical of his station, raised for the city or the professions via upright parents and a good school. But equally it had taken Sandra by surprise to be sure, and she wasn't certain at first what she felt exactly; shame, anger, amusement? But it was a kind of amused sadism, or scornful pity, that presently triumphed, naturally if surprisingly, over her competing emotions. She found that the spectacle quite turned her on, in fact, animating her sexually; a fact which was now evidencing itself in her increasingly sumptuous cackle. The sensation of her hard nipples rubbing lightly against the fabric of her light top was now productive of a deliciously crude pleasure.

She pulled out a pleated white mini-skirt from the wardrobe and held it up provocatively against her chest.

'What do you think Miriam, don't you think Bradley would look lovely in my little old tennis skirt?' Miriam merely smirked and nodded, sipping her wine indulgently. 'Come here Bradley darling,' Sandra instructed teasingly, 'Let me see how my little sissy looks in a skirt as well as my panties...'

Bradley, barely thinking at this stage, his swimming consciousness overcome with a tumultitude of contradictory sensations and emotions, and his cheeks burning hotly, couldn't bring himself to look his wife in the eye, but with the furtive glances he angled sporadically at Miriam returning only bemused and cynical sneers, he hesitated fatefully.

'Come on sweetheart...' Sandra cajoled gently, squeezing her bosom provocatively between her forearms and using the deep softness of her voice to lure him. 'Ah look, Miriam, he's gone all coy.' And she again laughed to her friend.

Without willing it, Bradley found himself crawling forward on his hands and knees toward her across the silken bedspread.

'Look at his pert little butt in my knickers!' Sandra went on, maliciously, 'We'll have to find a top as well, Miriam, to complete the outfit.'

When Bradley reached Sandra she instructed him to put her skirt on, which she then adjusted around his hips as if dressing a child. Then she put her hand up under his skirt and gripped his balls and manhood firmly in her fist, cupping his testicles with her fingers and squeezing his flaccid penis against them with her hot palm. She felt him growing involuntarily.

'He likes it Miri!' She squealed, appal and delight sparkling her tone in equal measure, 'See how his little tinkie squirms in his panties when I touch him!' Sandra laughed again, and pushed him back on the bed.

'Find him a top Miri, darling,' Sandra instructed. Miriam picked out a tight cropped t-shirt from a drawer, bubble-gum pink and designed to show off a woman's midriff, with the word 'Slut' emblazoned across it in shiny silver letters. 'Perfect!' Giggled Sandra, and they both cackled mockingly. Miriam moved forward to pull the top over Bradly's arms and head. He obeyed without a word. 'Now dance for us,' Intoned Sandra sternly, dropping her smile briefly as she directed her command, before grinning lewdly at Miriam. 'Wriggle about on all fours on the bed like a proper little sissy-slut,' she continued maliciously, 'I want to see your little ass squirm in my frilly little skirt.' Bradly did as he was told.

'I'm gonna make you cum in my panties,' Sandra told him purposefully, looking him right in the eye. 'Isn't he sexy, Miri, all dressed up in his wife's underwear? Wouldn't you like to see him cum in those beautiful wet knickers of his?' Bradley had chosen a pair of soft cotton, floral print bikini briefs, with elastic hems delicately frilled with lace. They were pink and yellow and red and orange, and hugged his cheeks and scrotum tightly, bunching his balls and penis together and restricting his straining hard-on which was tucked up under his ball-sack and between his legs. The material was bunching slightly between his butt-crack, and he could feel the elastic hem cutting across his buttocks. The sensation was acute, and delectable. He felt a bead of sweat trickle down his butt-crack.

Sandra was now rummaging around again in her lingerie drawer. 'Well what have we here?' She cooed provocatively, turning and shimmying up and down slightly, like an extra in a pop-video. Miriam's eye's widened. Sandra had removed from her drawer a large, elaborately moulded dildo. It was bright pink of various hues, and shaped like a penis, more or less, but with an extra protrusion at the base specifically designed to stimulate the clitoris. It had various sections of different textures, with what looked like beads or ball-bearings that would move and whir. She turned it on and it began wriggling and girating as though it were alive. The bulbous head swivelled ginormously at the top, turning in wide circles, while the bottom third, with the shiny beads beneath the translucent pink rubber, spun and rattled quietly. Three little rubber tendrils on the tip of the strange protrusion danced and writhed with a kind of alien grace. The whole thing vibrated perceptibly with a soft buzz. Then she turned it off again.

'I bet I know where you'd like me to put this,' Sandra teased, her voice rising as she wafted it teasingly towards Bradley on the bed, who seemed to both shrink from and lean towards it simultaneously, caught in a paroxysm of indecision. 'I bet you'd just love to have my giant cock in your arse, wouldn't you, you dirty little sissy boy?' She laughed, emphasising the word 'cock' deliciously. 'Well, let me see you suck it first like a good little girl. Like the good little slut you are,' And with that she proffered it toward him from her crotch, as if it really were her giant erect penis. 'Come on baby,' she intoned huskily, adopting her most sensuous exaggerated drawl, 'Come and suck on mummy's big dick!' She waved the dildo around vaguely, leering at Miriam as she did so. Bradley crawled towards her.

When he got to where she was standing at the side of the bed she thrust the dildo rudely into his face, forcing his lips open and shoving it into his hot, hungry mouth. He took it ably. 'That's it you little slut-whore.' She gasped, again suddenly surprised by the spectacle of her husband dressed up in women's clothing, kneeling before her pliantly and sucking away at the huge pink dildo like a ten-dollar whore. 'Eat mummy's cock like a good little sissy boy.' She motioned to Miriam to get behind him on the other side of the bed. 'I think Bradley here needs a good spanking, don't you Miriam, for being such a naughty little cocksucker?' Miriam just snorted again derisively, but she lifted his skirt up neatly and folded it gently over his backside. 'Shall I spank him Sandra?' She asked, nonplussed.

'Do you want that?' Sandra half whispered down to her husband, as he dutifully gobbled away at the big rubber dildo emerging towards him from his wife's slowly-gyrating crotch. 'Tell Miriam you want her to spank you, or I'll tell all your friends you like dressing up like a girl in my panties,' She added in a sudden after thought, 'Perhaps I'll have them fuck me while you watch, wearing them.' Bradly almost choked at this sudden surge of increased cruelty, but he managed to slip the dildo out of his mouth long enough to moan faintly, 'Spank me, Miriam. Please spank me Mistress.' A glistening string of spittle drooped from his bottom lip to the tip of the bulbous bell-end in front of him, and he descended upon it again in obedience to his wife's forceful hand on the back of his head. Miriam duly drew her hand backwards some distance before lunging it forward and landing a forceful slap on his right buttock. Sandra cooed in delight. 'Ooh! He likes it, he likes it!' She squeaked excitedly, her pert round tits bouncing up and down beneath her loose top as she jiggled on her feet. 'He likes being spanked like a little bitch!'

Then she leaned down close and whispered hotly in his ear, 'And now I want you to cum in my panties,' She instructed, again adopting the deeply patronising tone women use on pre-linguistic babies, 'I want you to fill those nice frilly knickers with your hot spunk, or I'm gonna have Miriam here tell everyone at your work how you like to suck on my cock like a little bitch-slut.' Bradley could feel his cock straining involuntarily against the tight material of the panties, and pressing against the soft skin of his bulging ballbag -- he hadn't cum in weeks and his testicles were full to bursting. 'Help him out Miriam,' Instructed Sandra, matter-of-factly. Miriam reached under him to cup his balls and penis expertly. She began kneading them rhythmically. Clenching her fists open and closed, and squeezing the thick flesh of his throbbing dick in her palm so that his mighty balls expanded and contracted between the gaps in her fingers.

'Suck sissy-boy,' Sandra ordered, and then mused, 'I wander what your boss would think if he could see you now? I'd just love to show him what I can do with you, and perhaps have him fondle my tits in front of you, while you're on all fours like a little slut girl, sucking away on my big dick. I bet he's got a massive cock, your boss, I'd love to feel it slip up between my legs from behind, and nuzzle at my pussy lips until it slides in all the way, as you take my dick in your mouth and jizz all over yourself in my knickers...'

With that Bradley came, extravagantly, splurging his semen violently into the sopping wet material of the panties, coating his balls and squirting hot sticky cum back up between his buttocks and over his rectum. Miriam yelped in mannered distaste, and pulled her hand away sharply. 'He's cum!' She exclaimed to Sandra pointedly. Sandra nodded and slowly pulled the dildo from Bradley's chomping jaw, his body sagging slightly as he fired the last couple of spurts from his constricted, aching member. 'Good girl.' Sandra coddled, patting his head gently and ruffling his hair. 'My good little sissy boy has cum in his panties, just like mummy told him to. Now let's see what else he can do.' And with that she beckoned him upwards with a hand on his chin, leaning down and kissing him briefly, playfully, on the lips, before motioning him round on all fours till his butt was facing her.

'Just look at the state of you!' Sandra gasped in exaggerated contempt, 'You're absolutely covered in spunk, you dirty slut!' She giggled raucously, and groped and fondled his sticky butt-crack through the material. She pulled the back of the panties down slightly around his buttocks, and he felt the shaft of the dildo begin to slide up and down the cleft of his arse cheeks, forcing his legs apart slightly and smearing the spunk about around his anus.

Sandra brought the now glistening member up to her face and examined it critically. 'Now who's going to clean this, I wander? Miriam, any ideas?' She laughed and tilted Bradley's head back over his shoulder by pulling his hair from behind. 'You've gone and got my lovely Rabbit all dirty, Bradley dear, and now you're going to have to lick it all up.' She said sternly, and wiggled the sticky dildo under his nose. Miriam reached out and took it from Sandra to stop her having to lean across the bed, before squatting down in front of Bradley. She set the dildo upright on the bed in front of him and held it at the base with her two sets of strong fingers. He could see his spunk dripping down one side of the big bulbous head. Miriam looked him straight in the eye and nodded slowly. 'Come on sissy-boy,' She whispered softly, 'Do what Sandra says and lick it clean.' Bradley slowly lowered his mouth over the shaft of the dildo, and began wrapping his tongue around it, slurping up his own jism obediently. The two women laughed patronisingly. 'Look at how he laps it all up like a good little girl,' Sandra smirked, 'Perhaps that'll teach him to go wearing mummy's panties,' And she shoved a finger abruptly into his rectum.

Bradley could feel his juices cooling around his exposed buttocks and cleft where the panties were pulled down slightly. But his balls and penis were still clenched snugly by the sopping material. The musky smell of his ejaculation was wafting up to him from below as he continued to slurp and suck hungrily on the huge fake penis in front of him. He liked the sensation of the springy rubber shaft in his mouth. Sandra motioned to Miriam. 'That's enough now, sissy boy,' she said, as Miriam passed her back the dildo. She flicked it on and off again quickly, as if to test the battery. 'You know what has to happen now don't you, for being such a dirty little bitch-slut? You can't go dressing up in your wife's lingerie, and sucking your own spunk off her dildo like a sissy, while her friend watches, you cheap little whore, and think to get away with it now can you? Not without being punished...' As she spoke she began working the giant penis head slowly into Bradley's rectum. Bradley bucked and moaned feebly, but he offered little resistance, and even pushed backwards on his elbows a little and parted his legs still further to better meet the intruder as he buried his face into the soft satin bedspread.

Once it was all the way in, Sandra paused with her hand on the button. 'Are you ready for this Bradley?' She asked, her voice flashing back to its regular aspect momentarily, 'Are you sure you want me to fuck you in the arse like a cheap little sissy slut?' Miriam smirked down at him and stroked him gently on the chin, nodding his assent for him. Bradley only managed a murmur. Sandra smiled. 'Good boy,' she uttered, and flicked on the switch.