James Thomas had always lived in the close. He had always walked past the big house on the corner, set back further than its neighbors, with high fences and dark blinds. He had always wondered who could live in such a scary place. The occupant was said to have an aristocratic heritage, keep her husband in service, and only leave her property under the moon’s light. Those insomniacs and voyeurs who had made out a silhouette in the early, quiet hours of a suburban nightscape described a tall woman with long dark hair and a great figure.

James Thomas was 18. He was a virgin, and this played on his mind more than anything else. He had spent his formative sexual years spying on his older sister and her friends at sleepovers, spying on neighbors through half curtains. The internet did not excite him, real-life did, but he was petrified of revealing his small manhood to anyone who might want to touch it. He had fooled around with girls but never had the confidence to pull down his last layer. He ached with desire and longing, but the only relief was his imagination and the bathroom sink, where he could watch his hand envelop his tiny penis and then wash his thick semen down the sink.

He was a quiet and compliant boy, diligent and hard-working, a loyal friend but consistently somehow average. He was handsome. Just shy of 6 feet, athletically built by hours of solitary weight training, and wearing a shock of light brown, some said the blonde hair. He was impeccably clean to the point of obsession.

On Saturday mornings, he worked in the local newsagent. Although he lived comfortably with his parents, his father insisted he pay for his ‘social extravagances,’ which did not usually stretch beyond drinks on a Friday. James Thomas was not a clubber or a drug taker, but he was more than happy to lose control with his mates at the weekend. Running slightly late, slightly flustered, just before 9, he was cantering past the house on the corner when he heard a scream emitted from its upstairs window. He paused and slowed to look. Nothing. He trotted on and listened to a man screaming ‘Nooooo’ and then a muffled noise and nothing. He looked around as if for confirmation, but affirmation was not coming. Conscientious as always, James Thomas felt obliged to do something. He opened the heavy rusting iron gate that he had stopped by. And taking a deep breath, strode in mock confidence up to the front door. It was ajar.

James Thomas searched for a bell. Nothing came to hand except a heavy whale-shaped knocker. He lifted the beast and brought it down against the heavy oak door. A flat bang and the door opened with a creak. Looking around again, James Thomas entered.

‘Hello, anyone there? Can I help?’ James Thomas passed through the sizeable open-plan entrance hall, turning to his left into what seemed to be a large dining room. But in place of the dining room table and chairs stood a solitary metal high stool and a small wooden cupboard in the corner. The room was lit overhead by a sizeable chandelier-like apparatus; dark blinds shut out the close and the world. James Thomas moved to the far end of the 15-foot room towards a distant door, calling all the time in not-quite-confident intonations. Suddenly he heard the heavy front door slam behind him.

‘What on earth do you think you are doing?’ Came the question before he could turn round. It was a woman’s voice but full, velvety, and distinctly public school.

James Thomas turned to face an apparition. Maybe 10 feet in front of him stood a tall woman in her late 30s in black thigh-high boots with extraordinarily tall, thin heels. Black lace garters and suspenders bulged slightly over shapely but still slender thighs. An impossible small skirt brought his gaze to an impossibly tight corset and spilling out of these two pale milky mounds, two firm full breasts that heaved slightly with apparent recent exertion. Her face was fixed, not exactly beautiful but entirely beguiling, angular, and full nose. Her hair was thick, sheen, and cascaded around her bare shoulders and arms. She held a riding crop in her right hand across her impressive chest. James Thomas took several sharp intakes of breath and felt his eyebrows come clean off his forehead.

‘Nothing. I errr. Heard something.’ He mumbled out and made his way, head down, towards his point of entry.

‘Not so fast, boy!’ She spat out “boy” with venom, and spittle flew towards James Thomas’s feet. ‘You realize you are trespassing on my property?’

There was a pause: James Thomas, head down, half-shrugged.

‘I have a good mind to call the police.’ The woman spat out again, rising slightly in her heels.

James Thomas lifted his head but didn’t make eye contact. ‘I’m sorry. I’m late for work. I was only…’

He was interrupted. ‘You were only what? You were only going to steal my belongings and rape me. I know your sort and where you live! You’re in for serious reprisals! I’m phoning the police.’ She made as if to go and fetch a phone.

‘No. Please don’t. I wasn’t doing anything. I’m not worth it.’ James Thomas said hurriedly.

‘Too right, you’re not worth it. Little bitch scum like you. If I don’t phone the police, you will have to do exactly what I say.’ The woman had marched over to James Thomas, raising her crop over her shoulder, he shrank back, but she merely let it leisurely rest on her bare skin. She fixed him with piercing dark eyes. They may have been brown, but he was confused that James Thomas could not tell.

‘Yes.’ He said.

‘Exactly as I say, or the police and your family will know what a thieving pervert you are!’ She seemed to rise again on her heels, taller than James just. He made fleeting eye contact and nodded. It was too late now, he thought. How would he explain his situation to anyone? He ‘heard something’ sounded like nonsense.

‘Then strip!’ The crop was swift across her chest again.

‘Pardon?’ James Thomas shrank away. The crop came down across his left thigh. It hurt. ‘Shit,’ he said, clutching his leg.

‘Now!’ repeated the woman.

James Thomas was panting and shaking and sweating. He made for his shoes first, slipping off his Converse and socks. Then went for the buckle of his jeans and undid his belt slowly, bending double to take off his trousers clumsily with quivering fingers. He paused when this was done with his pants in his right arm. The woman gesticulated to drop them with her crop and nodded to continue with his shirt.

James Thomas pulled his shirt gingerly over his head. He was shaking more than ever, and it was pretty tricky.

‘You’re slim. I like that.’ Said the woman with a hint of a smile. James Thomas smiled nervously. All he had on were a pair of old grey boxer shorts. ‘They’re rather loose around the crotch, aren’t they?’ said the woman. ‘Baggy even, as if there’s a lot of spare room. Show me your cock, boy!’

James Thomas hesitated. This was it. This was the first time since childhood that womankind would look at his birthday form.

‘Pull them off, boy. Show me your little package. Pull them down!’

Slowly and gingerly, James Thomas slid out of his boxer shorts which he left by his feet, quickly covering his genitals with his hands.

‘Hands away, boy! How would you explain yourself now? Naked in a woman’s house. I think you just got yourself in more trouble. Now hands away!’ The woman stepped within 2 feet of James Thomas. He could smell her heavy sweet perfume. He pulled away from his hands, folding them behind his head, and looked to the ceiling. He felt his penis was retracting into itself with his balls; he wanted to stretch it out a little but dared not.

‘It appears,’ said the woman in grotesquely sarcastic tones, ‘that you have a very small cock boy! What use is that?’ She was right by him now. James Thomas did not reply but felt his loins stir as this gorgeous figure hovered before his naked self.

‘What use, boy?’ The crop came down on his penis and balls. He bent double.

‘None. None.’ He gushed. But he felt blood rushing to the little shriveled piece that just jutted out above his testicles, enveloped by the sparse but gnarly pubic hair.

‘No wonder your pants were baggy. I think you would do better in a pair of panties. Don’t you? But what is this?’ As she spoke, James Thomas felt his cock grow hard. He felt it full of blood but dared not look. He was cringing.

‘You like it when you’re humiliated, boy! You and your tiny wank piece!’ She grabbed hold of my cock as it stood out and squeezed hard. ‘Look, I can barely see it now, and I have such small ladylike hands. You’re just a little boy! And what is all this fluff.’ She pulled hard on his pubic hair now. ‘And these baby bites. You’re hung like a baby boy.’ She now grabbed his scrotum and pulled up. Each time James Thomas writhed and blew air out of his mouth. ‘I think we need to tidy you up! Give you a boy’s haircut. Follow me, or else you’re in the national newspapers!’

James Thomas could do nothing but oblige. He followed behind her, grabbing a tantalizing glance at her bare pale pert buttocks jutting just beneath her skirt. He walked, and his hard cock bobbed, and he felt like a fool but more aroused than he had ever felt.

They came to a downstairs bathroom. The woman set about running a bath. She opened a cabinet and took out latex gloves, scissors, razors, shaving foam, liquid soap, and a device he did not recognize. The gloves made a load, exciting smacking noise as the woman fitted them over her hands. She ordered James to stand over the toilet bowl. Putting her crop to one side, she cut away at his pubic hair, ordering him to keep his hands behind his head and eyes straight ahead. James Thomas was soft again, and it was humiliating to have his small flaccid penis manhandled by a total stranger.

‘And your buttocks too. So much fluff, you little boy!’ The woman began to smooth shaving foam all around his buttocks and genitals. ‘Spread your legs and lean over the toilet. Eyes ahead, boy!’ She smoothed the foam between his buttocks, over his arsehole and perineum. His cock was hard again. ‘You like that boy! Having your arsehole touched. I thought as much.’

Then with expert ease, she shaved away. She had stopped the bath now, and within about 10 charged thrilling minutes, James Thomas was bald as his birthday suit.

‘Now in the bath. I don’t know where that dirty little cock has been or who’s been rubbing that little arsehole of yours.’ James Thomas climbed in. ‘Now wash all over.’ She stood back against the opposite wall. James Thomas looked to her again with confusion. ‘Eyes ahead, boy!’

He cleaned himself. He was good at that. He was still hard, and the sensation of his soft, smooth privates made him desperate to tug. But before he could dwell on the thought, the woman was by his side and had grabbed his hair.

‘That is mine now, boy. Do not dare touch your dirty tiny little pecker in my presence. You pervert! No on all fours. Now!’ James Thomas jumped to all fours. His arse felt cold and bare, and he felt embarrassed that this position made his cock look even smaller. The woman tugged his erect penis back between his legs. James Thomas drew in breath abruptly. Her hands were cold, but more than that, he thought he would ejaculate at any moment.

‘Fit to burst, hey?’ The woman said. She brought the crop down across his buttocks, nearly knocking James off his perch. ‘Not yet, boy. Maybe never! It’s mine now, your tiny micro-penis! Now I’m going to clean your dirty boy’s arsehole, which is also mine!’ The woman pulled out the black bulbous contraption; she filled it with warm water and a little liquid soap.

Suddenly James Thomas felt a finger probe his tight anus. It didn’t hurt, and it slipped in easily. He enjoyed the sensation and had experimented himself. His arsehole relaxed slightly. ‘You’ve done this before, you filthy fuck. Needs cleaning.’ She inserted a nozzle from the device into his anus and squeezed out the contents from the larger bulb at the other end. James Thomas was surprised at how pleasant the sensation of warm water in his rectum and bowels felt. She emptied the contraption then had him relieve himself over the toilet. James Thomas stole a glimpse of his captor’s cleavage as he did so; he desperately wanted to relieve his throbbing cock too. The process was repeated two additional times, and then it was back to the front room without a towel.

Shivering, his cock at last sagged, and he felt it shrivel to nothing. The woman smiled and stood, waiting for his cock almost to disappear. Then she was in the small cupboard. She came away with what appeared to be several cords of thin rope.

‘Lean over this stool. Now!’ James Thomas obliged.

James Thomas lent over the stool. Its narrow top came up to his waist so that he could rest his stomach on it with his feet still firmly planted on the ground. Its cold steel surface felt freezing against his already icy flesh. It shocked him a little, but he was set firm with a less than gentle tap of the crop on his bare, bald right cheek. What could he do now? He was entirely in the woman’s thrall. He had to submit in the hope that he might be able to walk free in due course, whatever that course that might be.

‘Now hold the legs. I am going to bind you. Do not move. Eyes dead ahead. Your dinky little cocklette is so shrunken and tiny now, like a frozen shrimp.’ The frozen shrimp received a firm strike from the crop, retracting further into James’s embarrassed abdomen.

The woman used the rope and bound his legs to their adjacent stool legs. The binding was tight but not painful, and with an efficient knot, they were firmly set. Then his arms were bound at the wrist. It was not painful and did not cut into his flesh as he had expected.

‘Now you are helpless. I wonder what the police would say if they saw you? Or your parents? Can you imagine?’ The woman paused. James Thomas kept looking straight ahead. The woman grabbed his hair and pulled his head back abruptly: ‘I asked you a question, boy!’

‘I don’t know. I’m sorry. I…’ James Thomas didn’t finish his sentence again.

‘Enough from you. No opinions. Yes and No. Now for your little shrimp head. I’m going to bind your little balls. Have you had that done before, you dirty pervert?’ The woman paused.

‘No.’ Replied James Thomas. A swish and the crop came down hard on his bare, smooth left buttock.

‘No mistress. Let’s get that straight little boy.’ She strung out the word ‘little’ and poked his testicles with the crop as she did so. James Thomas drew a sharp breath. She took another line of cord, thinner than before, and held in front of him. He was completely vulnerable, splayed over a stool, his firm goose-pimpled arse to the wind. James Thomas had no idea what to expect. He found himself petrified but also curious, even excited. He was in no way relaxed, but he found the woman attractive and commanding him in her uncompromising way rekindled suppressed passions for teachers and a mature dominant woman he had fantasized about routinely.

Suddenly his balls were being pulled downwards. This was not a delicate maneuver, but it was painful at once. As he began to recover his body temperature, he could feel blood diverting with his growing excitement at the intimacy. One firm hand pulled the little pair down, and the other turned the cord round and round the top of the scrotum above the testicles. It was tight, and James Thomas could feel the testicles themselves straining in the not-enough skin that had been pulled down. A glance between his legs revealed that the swollen pouch was turning a darker than usual pink.

‘Your cock is too small to bind. You may as well have no cock at all.’ The woman squeezed his cock in a fist. The exhilaration brought James’s penis back to life, and slowly he felt it swelling too. ‘That’s better, you little girl. Show me your clitoris bulge!’ She squeezed his penis hard again, and it became semi-erect, once more with a determined shake, and he was hard again. She let go, and his cock bucked and twitched, desperate for relief from this cycle of arousal and denial. The woman encircled his handful of inches twice with the cord. It weighed his thin cock down, but the strain of it, the tension, helped him stay aroused. But it was twisted tight, and again he could see his flesh turn a strange color, bulging through the cord as it dug in slightly. To heighten this stimulation, the woman had brought the two ends of the rope back under his perineum and then up his freshly-shaven crack to loop back over the buttocks and inner thighs. The rope was pulled in such a way that parted his buttocks, exposing his anus to the cold air. James Thomas felt the thrill of this new sensation and was sure his cock was dribbling precum. The woman tied the rope off after a couple more twists around his thighs. She noticed his dribbling penis.

‘Filthy boy. You best not make a mess on my floor. Here eat your filthy mess. She took her index finder and collected a tip coating. She held it up to James Thomas, who turned his head. ‘Eat!’ She said venomously. James Thomas kept his gaze averted. The woman grabbed the rope around his cock and balls from behind and pulled backward, pulling the whole apparatus back through his legs. James Thomas cried out. ‘Now eat!’ He obliged, licking her finger. ‘Suck it!’ He obliged again.

‘Now I know you like playing with your arsehole, so that I will block that off. It is mine, and no one shall have access. This is going into your arse boy!’ And from out of nowhere, a black tapering dildo with a flat base at one end appeared in front of James Thomas’s face. James Thomas fid enjoys playing with himself, it was true. He had even experimented with carrots and courgettes, but he had never had the gall to invest in the professional equivalent. The dildo at its fattest was certainly twice the diameter of an average supermarket carrot. ‘This is going to plug your dirty little arsehole. It is going to sit in there until I am satisfied. Do I make myself clear?’

‘Yes,’ Said James Thomas. His cock and balls were above his anus again. ‘Yes, mistress.’ The woman let them fall back into place with a swing that satisfied James Thomas.

Next, James Thomas felt a liquid sensation running down from the top of his crackdown through his parted cheeks over his anus and then drip off his perineum. He heard the fluid hit the wooden floor. It was lubricant.

James Thomas had felt the woman’s finger before, and again she gently eased it into his tight arsehole. His little pecker twitched as she did so, and he contracted slightly around her finger. The woman slapped his right cheek with a flat bare hand, and he relaxed his anal muscles. The woman repeated the entry, taking a little more gel each time. She turned her finger around in his anus, coating it. She then probed deeper taking more gel. James Thomas was breathing deeply and heavily. He could not deny that he was enjoying this, and he delicately tried to ease his cock against their ropes so that he could pleasure himself. The woman did not seem to mind his almost imperceptible gyrations and introduced a second finger. James Thomas gasped slightly at the surprise and felt the mild burn around the ring of muscle which left a pleasant tingling sensation as the pain subsided. Then the fingers were gone, and he could feel his anus dilated and coated in jelly.

James Thomas felt the unfamiliar hard plastic of the butt plug. It felt alien and strange but entirely erotic. This was a penetration of sorts, and he loved to feel his anus stimulated. The woman eased it in slowly, dripping more lubricant around the edges. Slowly she fed the device in, and slowly, James Thomas felt his arsehole consumed. Once the plug got larger than his usual carrot width, he wriggled in his bonds. ‘Slap’ came another bare hand on his bare buttocks harder than before.

‘Now, you are going to take this to prove to me that you have some ounce of manliness in you. Let’s not forget there is nothing between your legs to testify to it.’ The woman pushed firmly, but there was resistance, and James Thomas cried out. ‘Don’t make me gaga your other end too,’ she said. But James Thomas could not bear it, and he half-growled in discomfort. But he did not scream. He did not shout. Overwhelmingly now, he did not want this most intimate of his sexual experiences to end.

‘Right.’ The plug was removed hastily. And without warning, a black rubber ball was in his mouth like a chomping bit fastened around his head. It rendered his jaw completely immobile, and he dribbled out of his mouth as his protestations were muffled out. ‘Now this is going straight in, and no more moving!’

The butt plug was reintroduced to the entrance of his anus. This time there was a slight pause. The woman grabbed James’s cock with one hand and squeezed hard, ramming the plug hard with the other, seemingly with her whole weight. James Thomas felt seconds of burning agony around his anus, but it subsided after about half a minute. James Thomas had tears in his eyes, but he felt a new delicious sensation of being full-up. He clenched exploratorily around the plug. He could feel it stiff and smooth against the swollen vessels of his perineum, at the base of his now semi-erect penis. Without stimulation, the insertion had the effect of slightly deflating his erection. But he was thrilled by the novelty of it, by the excitation of however many nerve fibers he did not realize he had.

‘There. That is better. Much better.’ The woman pulled on the rope around his balls and cock again, letting the arrangement swing back to its resting position. She repeated this 4 or 5 times, and James Thomas could feel himself grow hard again and feel the end and inside of his erection swell against the hard object in his rectum. He felt he might ejaculate if the woman persisted. The woman sensed this and again wiped off his precum. The mouth gag was removed.

‘Taste your produce, your progeny, you filthy little cockles slut. Suck it all off.’ And James Thomas did so. ‘You’re about to cum aren’t you, boy?’

‘Yes, mistress,’ responded James Thomas.

‘Well, let me tell you that you will not cum today, my boy. You are not going to squeeze your dirty little sperm out of my little toy there. That is bound and out of bounds. But I like to see you excited. Do you like to be excited?’ The woman was on her haunches before him and let James Thomas and his eyes linger over her full breasts as they spilled over the top of her corset.

‘Yes, mistress.’ James Thomas unconsciously licked his lip, partly to remove the dribble accumulated but partly out of the pure erotic suggestion.

‘And would you like to see more of me?’

‘Yes, mistress. Please, mistress.’ James Thomas was breathing heavily, almost panting with anticipation. The woman half-smiled and turned away from him. She walked away, and James Thomas watched the perfect curves of her lower buttocks swing slightly pendulously, firm and smooth as they were. Suddenly she stopped. James Thomas felt his eyebrows raise reflexively again; he was sure he was flushing. The woman lifted her skirt and bent forwards. Beyond words, her molded pale buttocks were pert and high, with such flawless skin that they seemed milky. The woman bent forwards to touch the ground. She reached back and put her hand back between her legs. James Thomas could see her perfectly smooth vagina, pink and neat, and he could feel his cock twitching uncontrollably, and he sucked in his bottom lip. The woman spread her outer labia and slowly eased her middle finger into the glistening slit that was just visible. She eased the whole length, and James Thomas strained his neck to gain a better vantage.

The sound of gravel being spit up by car tires sounded outside. The woman spun around as if nothing had just happened. She walked over towards the door.

‘They have arrived,’ she said.

 

The End.

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.