Cruel Delilah: Real Adventures of a Cuckoldress

By Akasha

Delilah selected the posh downtown Hollywood hotel for a reason. It had a great location, a great suite with a view, and the lobby held a certain flair that appealed to her. She envisioned bringing many men there at one time in her life – but this time, it was really much more simple. There was one thing she wanted to do, and her slaveboy (well, man, really) was going to assist her with it.

This man – Brad – was a simple man, really. He was pleasant, classy, charming. He had traditional corporate good looks, a fairly decent body, but a pathetically small cock. Delilah liked to tease him relentlessly about this, and it always made her wet when he squirmed, visibly uncomfortable, as she stared and poked and laughed at his small member.

But Brad adored her and would do anything for her. That’s why they were such a good couple. Delilah was delicious, gorgeous and cruel – and Brad ate up every last bit of it, because he was a masochist and a pure whore at heart, and nothing thrilled him more than to see that delight in her eyes when she made him feel pathetic.

It was the second anniversary of their first date when she made Brad take her to the beautiful hotel. She wore an elegant sundress and sandals over her perfectly painted pretty toes, and he followed behind her a few paces with the luggage as she flirted with the bellmen and seemed to immediately have the young men drooling and watching her every move.

Brad could only watch and long for her attention. It was at times like this that he was reminded that she was the goddess and he was merely a tool for her – his devotion could only get him so far. At times like this it was like he did not exist. He was entirely forgettable. He just stood there next to the pile of luggage as two college-aged bellmen hustled around her to answer her whispers, not even acknowledging the existence of Brad.

Of course, when they realized he was with Delilah and the bags were indeed, hers, the boys climbed over each other to get to them and load them onto the cart for the ride up to her room.

“Nevermind that,” Delilah smiled behind her big sunglasses. “He’ll get my bags.”

This froze the tanned, gawking bellmen in their tracks for a moment, until Delilah added, “Oh, no. I still want you to come up. But he can carry the bags. You can open the door, dear.”

The bellmen looked at each other and pointed and chuckled, and one said, “Him or me?”

“Or both of us?”

“Him,” Delilah pointed. “You.” Her fingers touched the plastic name tag that read simple, “Jackson.”

“What a handsome name,” she smiled. Jackson blushed.

Brad pushed the cart that carried seven bags. Seven bags for an overnight stay. You could just never pack enough, Delilah would always tell him. Because she never knew what she would need.

Seven bags, and only one of them included any clothing.

Six bags, all leather, all toys, all devices. Brad held the cart as the elevator door closed, and he looked over to see Delilah smiling at Jackson, smiling at him as if he was prey. The sound in the elevator was simply the shuffling of his feet a little, the clearing of his throat, and Brad’s nervous, uncomfortable heartbeat.


Delilah did end up making Jackson unload the bags off the cart, telling the boy that he would need to earn his few dollars and that she wanted to watch him bend over. He blushed at the remark and kept looking awkwardly at Brad, probably wondering if the man was a driver, a lover, or a personal assistant. Brad was older than Delilah, who was older than she looked, but Brad had a forgettable quality because he’d become so good at being invisible when Delilah was prowling.

He was content to watch her, actually, because it thrilled him to see her in action, to see her start to get excited over the prospect of new prey. In no time she had the unassuming bellman in a bit of a trance, hoping to get laid, probably, but at the very least excited by the attention he was receiving from a beautiful lady.

Jackson took the handful of dollars eagerly, but really lingered in the room just to take in her figure and perhaps extend the fantasy a little. Delilah smiled at him and then told him she’d call down later to have him come up and move the furniture around. The comment made him laugh, but as he exited the room, his smile changed to a look of wonder as he realized she wasn’t joking.

After the door closed, Delilah snapped her fingers and Brad moved beside her, kneeling, absolutely on command, automatically. His eyes were shut at once.

She pulled up her dress, took him by the back of the head, and shoved his face into her pussy, pressing it tightly against the front of her panties. They were moist beyond words. He inhaled her scent.

“Jackson was nice to look at. Don’t you think?”

She was making a point to him. Brad got the message loud and clear. Her grip was firm, though, and it was obvious she was going to keep his face mashed against her panties, up against the lace, until little indentations appeared on his cheeks as if he’d slept wrong on the covers all night.

“I bet Jackson has a big dick” Delilah mused.

Brad could practically feel, smell, hear her getting wetter. Her fingers tightened in his hair. They tightened until he had to bite his lip to hold back a whimper.

Delilah appeared to be contemplating something, fantasizing out loud. “I bet young Jackson could fuck for hours, simply hours, and his big dick would feel so good in my pussy. Don’t you agree, tiny dick?”

The words hit him, went through him, made him shake a little. Brad was shaking and he didn’t know why. He didn’t want to get caught up in the wonder of why such humiliating statements excited him so much, because he wanted to enjoy the moment. He resigned himself to analyze later, as he always did, but never got around to.

Delilah’s grip tightened even more, and she parted her legs a little, inhaled, and said simply, “Tongue.”

This was Brad’s order to open his mouth and use his tongue, somehow, any way, to indulge her. It didn’t matter that her dress was up over his head, that her panties were still on. These were his problems. She was busy, he knew that, busy with her own thoughts – thoughts of Jackson’s cock. So he tried as best he could to get his tongue working under the elastic of the panties, or prodding over the top, doing anything to get close to her skin, to her clit, without disrupting her thoughts too much by banging her around with his head.

This was a delicate dance he’d learned many times. When she wanted tongue, he had to figure it out, and not bother her about it. He had to just obey, to find a way, and to hope he could do so in a manner that pleased her.

Her grip loosened a little on his head, a subtle indication that he was at least going in the right direction. “Yes,” she pondered out loud, “Jackson would be a nice fuck. But I don’t really have time for that. I have other plans for tonight. Plans….for you, Brad. You and your little cock…”

Brad’s eyes were closed, tongue was busy. He could hear the words, barely, as he pursued his task, trying so hard to please her, to make her more wet, to color the fantasy she was having by adding pleasure. It didn’t matter that she was thinking about Jackson’s cock, not his. All that mattered was that she was happy, and all that he wanted to hear were her moans of pleasure. At any cost.


Brad was hogtied on the floor as Delilah stood in nothing but stilettos, bra and panties.

She was walking across the floor with a big wad of money in her hand, many bills she’d pulled from one of the large suitcases as she unloaded toys, lingerie, outfits and devices, some of which he had never seen before.

Delilah started stacking the dollars across the nightstand, stopping to dance suggestively now and then, as the CD player in the room was cranked up with some alternative music that he found loud and somewhat obnoxious – but incredibly erotic when her hips were moving to it.

Delilah was in her own world, not even watching him struggle anymore (oh, how she loved to watch him struggle, sometimes just sitting and playing with her pussy for hours as he writhed, wriggled and groaned uncomfortably). She was stacking up the bills in a manner that looked like something out of a gangster movie when the bad guys were counting up their dough after robbing a bank.

The bills were crisp and stacked up nicely. Brad could not tell if they were tens, twenties or even hundreds.

“This is Brad’s money,” Delilah grinned, looking back over at him and giving him a nod which indicated that she wanted to see some struggling. Brad struggled.

“This is all Brad’s cash, and it’s here for a reason. Do you want to know what it’s for, Bradley bitch?”

Brad was afraid to ask, but he wasn’t gagged, so he went ahead and spoke. “What’s it for, Delilah?”

She smiled. Delilah walked over and lifted her leg slowly and deliberately, bringing it down to press her heel on Brad’s naked, tiny cock. “Oh, careful, I might smash that tiny little dick,” she teased. “Can my heel cover the entire thing? I bet it can. Does that hurt?”

Brad winced. He was used to this game, sadly. So many times Delilah had smashed, stepped on, poked and nearly punctured his penis with her heel. She did that when she wanted him to pay close attention to what she was saying, but it always did more to distract him. And even though he was struggling, hogtied, unable to protect himself as she pressed her spiked heel into his cock and leveraged it against his thigh, he found himself getting excited.

It wasn’t the pain or humiliation that excited him; it was the look on her face, the pleasure and amusement. She was glowing, electrified, excited, enraptured and he could tell her imagination was running wild with scenarios, ideas and plans that required a hotel room and seven pieces of luggage. This was unpredictable, cruel, insatiable Delilah.

He whimpered.

“The money is for tonight,” she continued, finally, now looking down on him to poke, prod, and pump her heel on and off his member, almost amused, experimenting. “I took thousands of dollars out of your account tonight because YOU – “she stopped to press deliberately hard right into the base of his cock, until he gasped. “YOU – are going to go out tonight, to Hollywood boulevard, and get me a hooker!”

Brad didn’t really hear that part, as the pain was making him shut his eyes tight, grimace, and see stars. But he felt her breath on his cheek when she crouched down, removing her heel finally, taking his chin in her hand and saying more clearly, “Brad is going to go out tonight and find me a MALE prostitute! And you are going to bring him back to the room and be a little bitch for me while I enjoy a real cock.”

Brad started to speak, and realized, half way through, that his words were a terrible mistake. “But…why don’t…why don’t you just call Jackson… he’s will –“Brad stopped and gasped in pain as he felt the familiar, ruthless grip of her fist around his balls. She gripped, squeezed, twisted and pulled.

“I don’t WANT Jackson. I want a WHORE. I want a streetwalker, with a BIG huge dick, and one that will do ANYTHING for money. Even more of a whore than you are!”

Brad got the message loud and clear, but he was still seeing stars when she rolled him over, spread his ass cheeks and started feverishly pumping her fingers in and out of his asshole – lubing it before shoving a large plug inside, then slapping his ass cheeks until they were red. Just playfully. Brad was breathing hard, his small cock fully erect to four inches, his ass pounding and his cheeks hot.

Delilah stood up and left him there on the floor as she mixed a cocktail, then stacked up the dollars into one large pile and went to the closet. “First, you will get me dressed. I want to be smoking hot for the male hooker, and while you get me ready, I’ll tell you what I want you to bring back. I don’t want to be disappointed, you see. I want your money to go to good use. And since you’ll be sucking his dick for me, I want to make sure he’s got a nice big cock. Even though everyone has a bigger cock than you!” Delilah burst out laughing.

“Untie yourself and then put on your pink teddy,” Delilah ordered. She bent over to release the one metal tie clasp that would allow him enough freedom to wriggle and writhe out of the hogtie. “Once you are dressed in your best cunt outfit, we’ll get my look together. We’re going to have such a nice evening!”


An hour later, Brad was playing wardrobe assistant while wearing nothing but a tight, uncomfortable, humiliating pink corset, thigh high stockings and lace panties. Delilah lounged in main part of the suite and smoked a cigarette casually, making a few phone calls to girlfriends and occasionally barking a seductive order.

Brad hustled, keenly aware of his uncomfortable erection in the panties and the too-tight feeling of the plug as he moved around the room. He heard her in the next room as he rummaged through the large closet, trying to find the boots she had described to him. He could hear her calling room service and ordering a bottle of champagne.

Next, he heard her instruct the room service staff to have Jackson bring it up, then he heard her provide explicit instructions about it, making sure they were aware of her account with the hotel, her connections with the hotel manager and her status. It did not take long for him to realize how much the wait staff was going to be hustling, which meant in no time Jackson would be knocking eagerly at the door with the room service cart.

Immediately Brad was distracted, horrified, mortified, at what he knew Delilah was up to. He sheepishly brought the boots into the next room and she shook her head. “Not those ones. You stupid bitch. Get me the leather boots. Then go answer the door. There will be a knock momentarily.”

Brad wanted to sink into a hole and disappear. “Can I put on some clothes?”

“You’re wearing clothes.”


Delilah laughed and put out her cigarette. “Fine then. I will answer the door. You go run off and hide in the closet then, and don’t come out until I tell you that you can. Remember, this was your choice, Brad!”

He watched as she made her way to the door. Delilah was now dressed in only smoking hot black lingerie, high heels, her make up and hair done dramatically, her body smashing. When she opened the door in that to the waiting Jackson, he’d be ready to die on the spot, sure he’d died and gone to heaven, and Brad would be curled up in a ball hiding in the closet until she was done – which could be hours.

It was that, or answer the door in pink lingerie with a tiny erect penis popping out of a too-tiny thong, humiliated, as Delilah laughed and pushed him aside and probably made some cruel comment.

Ironically, it was impossible for Brad to determine which scenario turned him on more.

Dejected, he retreated into the closet and closed the door, mostly because he did not want to risk offending Jackson with the sight of his large, bulging body in the pink lingerie. Instead, he found himself surrounded and assaulted with the scents of Delilah; her leather wardrobe, the various pairs of panties, many still wet, tossed inside the confines of the closet. Dirty lingerie, black shiny rubber, and an assortment of toys joined him in the cramped space. He heard the popping of the champagne bottle, the deep laughter of a bellman obviously pinching himself because he was sure he must be dreaming.

Then he heard the familiar moans of sweet Delilah being fucked; she choose the place on the floor right next to the closet, her legs probably up over her head, and by the sounds of it, Jackson did have a huge, wonderful cock.


Brad counted four orgasms and three positions, and it was more than 90 minutes before Jackson was allowed to leave the room. Not until she tipped him though – with Brad’s money.

“Holy shit,” he heard the young bellman exclaim. “I can’t take that.”

“Take it,” Delilah ordered. “It’s not my money, it’s my boyfriend’s.”

“I can’t take two thousand dollars! That’s not a tip, that’s — “

“Take it.” She ordered. “I insist. I get wet when I use my man’s money that way.”

Brad shut his eyes tight. He realized he had jumped the gun – they weren’t over at all. They were just getting started. He heard the familiar sounds again, kissing, moaning, and then fucking. This time, Jackson lasted 30 more minutes.


Brad fell asleep in the closet but awoke with a start when Delilah opened the door. He came pouring out of the closet as he was leaning against the door, waking up when his cheek hit the ground.

She laughed out loud. Brad looked up to see her standing there, disheveled a bit but still beautiful, holding a glass of champagne. She opened her legs a little. “Cum’s dripping down my thigh. Lick it up,” she said. It was so matter-of-fact for Delilah.

Brad struggled, cramped from being in the small space, but managed to kneel upright and move his face to her leg and open his mouth, letting his tongue lap up the creamy clear-white fluid that was indeed trailing down her thigh.

“I saved some champagne for you,” she smiled, reaching to the countertop and taking the glass that was placed there.

Brad looked up, licking his lips, tasking the young man’s cum. He did expect her to have a glass of champagne, but realized all too quickly that of course that’d be too easy. Not Delilah.

No, she had a glass in her hand for him, and a smile that made her look like she’d just won the lottery – pleasantly fucked, glowing, gloating. And in her hand was a champagne flute for him.

Half full of cum.


Part of Brad thought maybe Delilah had “spent” enough money and got what she wanted out of Jackson and would dismiss the dreaded hooker idea, but he was mistaken. In no time, after watching him lick clean the glass of Jackson’s cum, she was ordering him to help her freshen up and providing him a list of criteria for his male gigolo-expedition.

She was explicit about what she wanted. The male prostitute had to be young, built, have a huge cock (black would be ideal, if his dick was humongous, although “Any guy looks huge next to your little pecker”), and be clean in appearance, not a junkie, no drugs, and not look or act gay. Delilah told Brad that if he came back empty handed or came back with a guy who looked like crap, was a street whore or drug addict, she’d spend the evening kneeing Brad in the nuts until he cried like a little girl. He knew she meant business.

After much begging, Delilah did allow Brad to put some clothes on over his lingerie. She was going to tell him no, after all, the transaction was going to be made from the safe confines of his car and the gigolo would not see his cute pink teddy until he got in the car anyway. And who cares – Brad was a paying customer. But he pleaded with her, and she let him put on shorts and a t-shirt that barely covered him up.

Delilah gave him a time limit of one hour and as he left she was curling her long, beautiful brown hair, sitting at the vanity in nothing but a short cami and black thong panty. Her hot outfit was on the bed, ready for her, and her shoes were lined up perfectly so she could make a selection. The stacks of twenty dollar bills were still lining the dresser table.

Off Brad went, horny and leaking, to scour the streets of West Hollywood in search of a young, hot, hung stud with a big cock so his lovely Delilah could pay him to get his dick sucked.

He had never been more turned on and ashamed.


Brad “shopped” intensely with Delilah’s instructions in mind, wanting so desperately to bring home a prize she’d be pleased with. He found himself looking at the prospects in a manner that seemed to excite and arouse him as he was thinking so much of her pleasure and satisfaction. It became surreal how much looking at these men made him hard and horny and how he found himself imagining the feel of their dicks in his mouth. But mostly he was imagining her wonderful, pleasing moans of ecstasy as she watched and participated. He felt the panties getting incredibly tight, making it uncomfortable to drive.

Nervously watching for police, Brad leaned out his window and awkwardly conducted quick interviews with the laughing, smoking male hookers, some of whom took a liking to Brad at once, probably because of his Mercedes and look of wealth. But the ones that approached him seemed too gay, and he knew Delilah didn’t want that. So he pressed on, getting more nervous and worried as time ticked by.

He imagined waiting Delilah, back in her room, legs open in the large chair at the vanity, playing with herself in the mirror. Delilah liked to masturbate in the mirror, sometimes she would make Brad watch her while she watched herself, her toes curling into the mirror as her legs were up on her own vanity at home, her pink vibe sliding in and out, deep and inside, her hips thrusting as she wailed in pleasure.

Brad stopped himself as he tensed and twitched uncomfortably, awkwardly in his car seat. He stopped at a corner and looked out, spying a younger looking, tall, dark haired man standing nearby. The man caught his glance and walked over, leaning down, smiling. “What’s your name?” he asked in a deep voice. He looked European.

“Brad,” was his response. He stared at the handsome gentleman – he knew his dark, European looks would please Delilah. “How old are you?”

“Old enough,” the man smiled. “My name is Jeremy. Can I get in?”

Brad nodded, and Jeremy came around and got into the car. He was in jeans, a leather jacket, nice shoes. He didn’t look like he was homeless. He was wearing a nice watch and some jewelry.

“You a cop?” Jeremy asked, still pleasant, smiling, very casual.

“No,” Brad responded, watching the young man put on his seatbelt.

“Then let’s go,” he said, leaning back into the seat, admiring the inside of the automobile.

Brad was excited. He could smell a little bit of cologne. Jeremy looked clean, presentable, and he had a big, thick bulge in his jeans. Brad thought about asking how big he was, just to be sure he’d meet Delilah’s satisfaction, but even the outline in his jeans told a story. Besides, he only had fifteen minutes to get back to the hotel, and he could not keep his Mistress waiting too long.


Brad could not find a way to explain anything to Jeremy, who occupied his time adjusting the car radio, singing a little, and then sending some text messages on his phone. Jeremy said something about five hundred dollars and condoms and Brad just nodded and said that was fine, focusing on his car speed and the urgent matter at hand.

Brad’s heart was pounding, so nervous, thinking of what Delilah would think of the prize he was bringing back to the hotel. His mind wandered to what it was going to be like when he sucked the strange man’s cock, and if Delilah would let him use a condom since the man was a whore. He wondered if she was going to fuck the hooker in front of him and make him watch, and how much she would humiliate him about his small penis and inadequate abilities in bed.

Nothing really mattered, though, except the smile she would have and her pleasure, her amusement in the evening. Brad knew that Delilah clearly was electrified by this fantasy and reality and was probably well on her way to her third self-inflicted orgasm by the time her brought Jeremy through the lobby and to the elevator.

“You in town on business?” Jeremy asked as Brad pushed the button for the 17th floor.

“Kind of,” Brad responded. When the doors closed, Jeremy reached over and put his hand on Brad’s crotch, making him jump and push his hand away. It was unexpected and uncomfortable.

“Easy, there,” Jeremy laughed. “Sorry. First time? You straight? Curious?”

The door dinged. Brad cleared his throat. He wondered at that moment if he really knew what he was getting himself into.


Brad was obviously ten times more nervous than Jeremy (who was not nervous at all, not that Brad could tell at least), but then again, Brad had a lot more on the line than the hooker did. If he disappointed Delilah, it would be a long night. It was going to be a long night anyway, with cruel Delilah, but disappointed Delilah was an entirely different dilemma.

By the look on her face, Delilah was not disappointed. Brad took her all in as if seeing her for the very first time – she was simply captivating, so beautiful, so sexy, wearing a tight black dress, showing off fine toned legs with sexy five inch heels. Of course, Jeremy was gay, or at least presented himself as gay, so he probably was not as impacted – more so, he was kind of puzzled.

“Well, aren’t you a handsome thing,” Delilah smiled and walked over, holding out her hand to make an introduction. “Delilah,” she beamed, looking the man up and down slowly, tilting her head slightly to take a longer gaze at the visible bulge in his jeans.

“Jeremy,” he smiled back, then looked at Brad, curious, put his hands in his pockets, and said “So what’s going on?”

“The shower,” Delilah instructed, and put her hands on Jeremy’s shoulders, spinning him toward the bathroom and giving him a shove. “You’re getting cleaned up, then Brad is going to suck your dick, then you are going to fuck me.”

“Cool,” was Jeremy’s simple response, as Brad felt twitching in his panties, a flushing warmth in his cheeks, a familiar tension building in his frame. The plug was still nestled tightly way up into his ass cavity, and the shuddering in his bones made the plug even more uncomfortable and ever evident. He stood there, unsure of what to even do with himself, as he heard the water come on in the bathroom shower and some laughter erupting.

As if on cue, Delilah emerged, taking off her earrings and slipping off her shoes. It was clear she was going into the shower also. In a moment, her dress was off and she flung it at Brad and the fabric slapped over his face. When he pulled it down, her panties smacked him in the face. “Hang up my clothes, bitch,” she ordered. “Then get undressed, down to your sissy lingerie, kneel down, and wait by the bed sucking on your large dildo like it’s a pacifier. See you in twenty minutes.”

And that was that. Brad stood there, holding her dress, her stockings, bending over to pick up the rest of her clothes and lingerie as he watched her naked, perfect ass dart into the bathroom. She left the door wide open so he could hear everything, of course, from the moans to the laughter, the splashing of the water, and her commentary on the size and thickness of Jeremy’s perfect cock.

Brad, now in nothing but a too-tight pink ensemble of sissy lingerie, found himself kneeling bedside as instructed, sucking a large, thick flesh colored dildo obediently. Up and down he went, sucking, slurping, eyes closed, concentrating on it, realizing that soon he’d be deep throating the entire length of Jeremy’s perfect dick as Delilah watched. Maybe she would circle around him and give instructions, reaching over to poke at Brad’s miniature erect penis. Maybe she’d stand behind him and spank his ass with a paddle to force him to go deeper. Or, if she was in a certain mood, she’d just sit there a few feet away and masturbate with her thin vibe, cumming again and again as the well hung man came all over Brad’s face or in his mouth.

As usual, Brad had no idea what his fate would be. He just remained kneeling there, reaching down occasionally to shift his small package in the too-tight panties, trying to assemble some level of comfort despite the growing fear and dread mixed with anxious excitement.

If nothing else, his jaw was clearly now stretched out and he was ready to accommodate Jeremy’s dick after twenty five minutes of practicing. So when the man emerged from the shower, a towel wrapped around his waist and Delilah trailing behind him naked, he thought he’d be ready.

Truth be told, Brad was never ready. It was always like the first time again.


Delilah crouched down and got close to Brad’s face, and her smile illuminated his world. He could smell wet pussy, it was as if her arousal seemed to permeate her entire being when she was that hot, that full of lust. Indeed, she was full of lust – lust for Jeremy, the gorgeous, perfectly built hooker who was there for $500 an hour. $500 an hour of Brad’s money.

Delilah smiled her big, pleased grin and put a finger under Brad’s chin. “Is tiny dick ready to suck a real cock for me?”

Brad was staring at Delilah, shaking a little, barely aware of the presence of another man in the room, who was off behind him pouring some champagne or inventorying the gear that was spread out everywhere. Maybe he was admiring the tall stack of twenty dollar bills that sat on the dresser.

Delilah went into a nice, long, humiliating diatribe about how large Jeremy’s cock was, and how excited she got in the shower when she was able to hold it, feel it against her skin, and tease her pussy with it. Because, after all, she was rarely around such a big cock!

She emphasized this by reaching down and pulling Brad’s pink panties down a little, then poking his erect member with her fingernail. “Is it hard? Is that it?”

Jeremy was chuckling somewhere in the background, seemingly unaffected by the fact that the man who picked him up an hour earlier was kneeling with a dildo in his mouth wearing nothing but a woman’s set of pink lingerie as Delilah poked his penis with her fingernail and called him “tiny dick.”

Brad reminded himself that as a male hooker, Jeremy had surely seen worse. Somehow that did not make him feel less degraded and humiliated though, as Delilah turned around and addressed the gigolo, asking if he’d like his dick sucked or wanted to wait, asking if he wanted to piss on the sissy bitch in the bathtub because she looked good soaking in golden pee, or if he just wanted to fuck Delilah doggy style right there.

Jeremy appeared, hands on his hips, still in nothing but a towel. His hair was wet and disheveled, and the water droplets were dancing across his chest illuminated by the light in the room in a way that made him look like something out of a modeling photo session. Brad realized that the man’s features were, at worst, nearly perfection. His smile was subtle and handsome, he had perfect teeth, and his biceps were built and solid. Out from under the dim lights of the dark streets and now in perfect lighting, it was clear that Jeremy was a 10.

When Delilah reached up and pulled the towel down away from Jeremy’s hips, Brad realized his looks weren’t the only 10. The man’s cock had to be ten inches long, and thicker than even the monster dildo he’d been practicing on. His eyes fell on the large dick and he was entranced, intimidated, and incredibly humiliated.

Delilah slid her hand up and down the thick cock as she stared at it with admiration, cooing. “Isn’t that the most magnificent cock you have ever seen, Brad?”

He just swallowed, and managed to croak softly, meekly, “Yes…yes, Delilah.”

Jeremy chuckled, obviously not the least bit uncomfortable standing there naked. Then again, Brad reminded himself, if he had a body like that he wouldn’t be uncomfortable standing there naked either.

“Suck it,” Delilah ordered, and Brad’s train of thought was broken at once. The command, the tone of her voice, everything about her attitude snapped him into obedience like nothing else. In a flash, he had the man’s cock all the way in his mouth and was bobbing on it, choking on it, eyes shut tight and watering.

Brad focused on the pleased, content commentary Delilah was making, and tried to ignore the deep moans and feeling of the man’s hands on his head as he sucked the cock. Delilah asked Jeremy how long he could last, and he said “All night baby, all night.” Brad choked and kept sucking, his jaw already burning and aching, the drool already dripping off his chin. Precum filled his mouth a little at a time, mixed with his own spit, and he was nearly in a trance soon, listening to Delilah as she obviously pleasured herself.

Licking, tasting her own juices, playing with her pussy, locating her vibe, exploring her clit, playing with herself, touching and teasing her nipples, encouraging Jeremy, “Deeper, deeper, fuck his face, fuck his face hard! He’s a cunt, fuck his mouth harder!”

Brad’s head was spinning, his mouth stretched and sore, eyes shut tight. He felt like the center of the universe and kept reminding himself it was all for her, all for her, all for her pleasure, trying to forget that a man’s dick was in his mouth and it was throbbing, pulsing, and could explode at any time and fill him up with cum. Visions of cum dripping from his mouth, gagging him, choking him, or coating his face all haunted him for a moment but he kept sucking hard, listening to Delilah moan and coo in pleasure.

While his head was spinning, Brad was barely aware when Delilah pulled Jeremy off of him, away from his face, then flopped the hooker over onto the bed. Apparently, that was that. Brad just remained kneeling there in his pink lingerie, his lips throbbing, his panties tight and wet, as Delilah pounced on Jeremy and in one fluid motion crawled over him and reached into her bag for a condom.

The next thing Brad knew, the condom wrapper slapped him in the face and Delilah was giggling, and Jeremy walked over, his big cock glistening and bouncing right in his face.

“Put the condom on him,” Delilah ordered, now on her stomach on the bed, her chin in her hands, as if watching a little show. “Little bitch, put the condom on the real cock. Use your TEETH!”

Jeremy laughed and said something but stood there patiently as Brad fumbled with the condom wrapper and tried desperately to do as told, perhaps experiencing the largest dose of humiliation ever as he used his mouth to carefully place the condom on the large cock. The condom was too small.

After a few attempts, the humiliation overwhelmed him. Jeremy said, “Whose condoms are these! They are too small.”

Delilah laughed out loud and came over to investigate and responded, “Oh my God. These condoms are too big for Brad. That’s hysterical. Oh shit. Bitch you might have to go get some bigger condoms!”

Brad felt a sickness come over him, realizing he might be shopping late at night for condoms, and of course Delilah, in her current mood, now totally turned on, would surely make it a totally degrading experience.

“No I got some,” Jeremy said, turning and walking over to his pile of clothes. Of course, Brad realized, the man traveled with his own, large sized condoms. At least he was a safe hooker.

In a matter of moments he returned, but instead of taking the chance to slip the condom on himself, Jeremy shoved the wrapped in Brad’s mouth, obviously enjoying his humiliation just as much as Delilah was. Once again, he found himself fumbling with the condom, trying desperately to put it over the large, thick cock with his mouth.

“Go ahead and suck on it a little for good measure,” Delilah ordered, now watching as she played with her pussy, her hair also disheveled, her fine body glistening with perspiration and hot sex.

Soon the taste of latex filled Brad’s stretched mouth, and he gagged a couple of times as Jeremy pumped his hips harder, making sure the full length of the shaft entered the slave’s mouth.

“Suck his balls, whore,” Delilah ordered. She clearly was now in the mood for a show, before she was going to get fucked, and that could take all night, Brad knew. So he went ahead and obeyed, taking the large heavy balls into his mouth one at a time as the man groaned and panted, complimenting the slave on what a good cocksucker he was.

Time became a blur and he lost track of everything, so much so that he was nearly in a different state of mind completely when Delilah once again pulled the hooker off of him and brought him to the bed. She proceeded to first fuck him by straddling him on top, but when his cock proved to be too large, they switched to missionary and finally doggy style, then back to her on top.

Brad just remained on the floor obediently, watching, humiliated, as the man pleasured her with his large cock over and over again. If he was indeed gay, he was quite convincing, because his hands enjoyed every inch of her beautiful body and he moved perfectly against her small frame, holding her by the hips as he penetrated her again and again.

When he announced that he was about to cum, Delilah encouraged him to cum inside of her. Brad was relieved, for a moment, because he had worried she’d make him cum on Brad’s face, a little trick she loved. But the hooker did cum inside of her pussy, a place Brad had not been in months. He could only fondly reflect on the memory, before she confessed to him that sex was not enjoyable because she could not feel him inside of her due to his tiny size.

Giggling, spent, panting, Delilah rolled over on top of Jeremy, who was panting also, and slid the condom off his cock. A huge load of white cum filled the tip and the entire condom was slick and disgusting. Brad watched, mortified, as she carried it over to him. “Want to taste my pussy, Brad?”

How could he answer such a question? It was the ultimate trick question. The question was designed to be his undoing. But he could not lie to her. “Yes, Delilah, I want to taste your pussy.”

“Open wide,” she ordered, holding the condom with two fingers as if totally disgusted, looking at it with a wrinkled nose but a huge smile. “Open up and get a big taste!”

Brad shut his eyes tight and opened his mouth obediently. Soon his tongue was heavy and he felt a big, thick glob of latex, pussy and cum in his mouth.

“Chew it, suck it!” she ordered, holding his chin closed. Her hands were warm and smelled like pussy, like sex. He felt cum oozing into the corners of his mouth. The taste of pussy was there, but mostly, it was all mansex and sweat, and the thick, slick taste of a large load of cum that was not his own. He started to gag.

“If you spit it out or throw up you are drinking a pissload!” she threatened. “You know how much I would love to see it washed down with a load of piss from him.”

It took all of Brad’s resolve to not throw up or spit it out. He kept his eyes closed and focused on the taste of her pussy, however faint it was. She made him sit there for quite some time until he sucked and chewed the condom. Then she threatened to make him swallow it and had him about to do it before she laughed and told him to spit it into the trash.

Jeremy was up and back in the shower, and Brad was not even aware of hearing him get up or go there. The clock read 4:35am. His cock was aching in the tight pink panties and his knees were sore. Delilah was flitting around the room on cloud nine, listening to music, dancing naked, then admiring Jeremy as he toweled off in the bathroom doorway.

For the final humiliation, Delilah came over and ordered Brad to pay the hooker. She picked up the large stack of bills, Brad’s money, and shoved it into his hands. “Crawl over and pay the prostitute and thank him for letting you suck his dick and for fucking your girlfriend the way she deserves to be fucked – by a real man!”

Brad looked at the stack of bills. Hundreds, thousands of dollars. He crawled over to the hooker, who was standing there naked, his thick cock erect again already. Jeremy was smiling with his arms folded over his chest, amused.

Jeremy looked past the kneeling man and listened to his little speech, then nodded at Delilah, “I don’t have to leave just yet, you know. You want to go again? You want to party?”

Delilah walked over and Brad felt her hand behind his head, her fingers twirling in his hair. “That’s ok dear. I enjoyed it, but I need a little alone time with my whore now. Even tiny little dicks need attention now and then, after all.”

Jeremy chuckled and took the wad of money, stuffing it into his pocket. “Your call,” he smiled. “Thanks. See you around.”

With that, he started to collect his clothes, and Brad found himself feeling warm, content inside. Not because of the extreme humiliation that always cleansed him and made him feel so raw and alive, but because of the nurturing feeling of her fingers in his hair, and the contentment he felt as she sent the perfectly chiseled man with the huge cock away so she could spend time alone with her slave.

To reward him, maybe. Maybe she would let him cum, or let him taste her, but maybe not. Still, the moment she sent the third man away was always the time he felt whole again, realizing the bond they shared. After all, Jeremy was the one pushing the button on the elevator, and Brad was the one curled up at her feet.

©, used with her permission. For more of her Femdom erotic visit her site Akasha’s Web.

Originally posted 2009-03-05 09:13:36.

No Erections in Penis Prison

Mistress Locks Up His Penis


She stroked me to waken and reminded me she hadn’t let me cum last night, or the one before, or for a long time. “How long has it been since you’ve cum?”

“6 1/2 weeks I said.” She took my balls gently and asked again more firmly, “Do not lie to me. I want the truth. Have you really been completely chaste all this time?” “Yes Ma’am, I have really.” I pleaded.

“I know you play with it all the time. I know you get hard during the night and I’ve seen your hands move toward playing with it with me right next to you. You don’t really think I believe it’s an accident when you “find yourself” between my legs do you? It’s not, IS IT?”

“No Ma’am,” I pleaded when she squeezed my balls hard. She released with an order to get out of bed, get her coffee and bring it back with her hairbrush. I started to say something but resigned myself, this was what we’d agreed to. I had asked her what she thought of Femdom and when she admitted it intrigued her, I confessed my secret yearning for it. In one evening a few months ago I went from casually asking her opinion to begging for her dominance and pledging myself to her discipline.

She nodded to the nightstand and I set her coffee there. Propping her back up on pillows, she held out her open hand for me to hand over her hairbrush. Ordering me to kneel on the bed in front of her, she raised her knees and used one foot to tease my penis to a fast hardon.

“I know you haven’t cum and I appreciate your honest effort Sweetie, but to tell the truth I’m not completely satisfied. Are you?” “Yes Ma’am i am because…” “SHUSH!”, she cut me off, “Yes Ma’am or no Ma’am will be sufficient. And another thing, stop moving and rolling your hips around at me. You are not playing with my foot, I am playing with your penis. Is that understood?” To which I began a long series of Yes-Ma’ams.

“Do you want to do as you’re told? Do you think you can? I doubt it, you’re hard right now and you are under specific orders not to get hard without asking permission, right? Listen Sweetie, when I told you I wanted to control all of your sexual pleasure and make you dependent on me for all of it, you begged me-BEGGED me to make your penis my slave. You recall? Did you mean it? I thought so and fyi, I like having a penis slave and have no intention of ever giving it up. You like that thought don’t you? Yes, it would seem so by its response.”

“Did you use the rest room while you got my coffee?” she asked matter of factly. I had. “Well I didn’t. Lean over and you can be my toilet again this morning. Do-not-spill-a-drop-understand!” This new twist was getting more habitual, and I was pretty sure she intended to keep on using me for her toilet on a a fairly frequent basis. Two things were obvious. She was getting more and more sadistic in her sense of dominant degradation and I was sinking deeper and deeper into humility before her. Which I guess is what we wanted.

She finished and ordered me back to my knees. “Now, before we get back to my hairbrush all over your bottom for last night, here’s what I’ve decided to do about your penis from now on. Since you can’t or won’t control your erections, I’m going to go ahead and lock it up.”

“I’ll be using a real cage that will never even allow erection while you’re in it. It’s a real lock and a real key and I will have it and you won’t. The rules are getting simpler. Your behavior has landed you in penis prison. Once I lock you in, your only way out will be when I’m in the mood to tease you. And from now on, your penis will truly be my slave because every time I unlock it, your hands will be cuffed behind you. You will never be able to play with yourself. My hands will be the only hands you feel and the ones you’ll go crazy begging for.”

“Oh Sweetie I know! I see it in your face. I know you’re scared about submission you can’t escape. I know you want it too. I can tell by the way your loins are almost gasping for breath. Do you want to cum right now. Go ahead, this will be your last…Don’t touch…No…I won’t either. This is your last chance if you want to cum go ahead…

…Okay Sweetie that’s enough…I love you for trying but that’s ok. I’ll take care of your penis from now on. Now I want you to lie on your back and eat me while I put this on you. You’ll have to lose that erection or I’ll have to use these hairbrush bristles to get rid of it for you.

Women With Whips & the Men That Worship / Fear Them

Submissive males, slave men and their Domme’s whip.


Some crave whippings badly and seek only the most sadistic women. Some masochists are so insatiable that they are never satisfied. These often join the ranks of smart-assed masochists. Some are willing to risk being maimed for that pain they believe will be the greatest experience of their lives.

Man submissive men fear the lash. They don’t eroticize pain. Lucky ones serve a woman who only whips men when the deserve punishment. Or use other nonphysical punishments. Should he worship a sadistic woman surrendering to her pleasure in cruelty may be a constant challenge to his capacity for submission.


Fortunately most submissive guys’ sadomasochistic orientation isn’t so polarized.

Chaste Engagement

Linda had been my girlfriend since seventh grade. I loved her so much. I’d do anything for her.

.I’d never pressured to have sex with me. And I’d held myself pure for her sake.

It hadn’t been easy. And it was getting worse. That was one reason I decided to propose to her.

I was still on my knees waiting to her here response. She smiled down at me.

“What a good boy you are Eddie. I figured it wouldn’t be long before you did the right thing.”

Figuring that meant yes I started to rise. She pressed the back of my neck, holding me down and told me to wait.

She went to her dressing table and brought back a small box.

“I’ll wear your engagement ring if you’ll wear this for me.”

“Sure, whatever you want,” I never could refuse her anything.

I thought she’d show me a ring but it was a jumble of plastic and metal.

“I know you mean to always be true to me. But a girl has to make sure. This is a chastity belt for a man. You will lock yourself up and I will hold the key.”

I was stunned. This wasn’t what I expected.

“I know you masturbate. Don’t blush. You are a male and can’t help it. But if I am to be your wife you should save it all for me.”

We couldn’t possibly marry for a couple of years!

“Will you do this for me. Don’t worry, when my husband and are well behaved I’m sure to let you out at least once every month or two. Probably at least a couple of times on our honeymoon. Don’t you want to do this for me?”

I never could say no to her. Not even now.

Originally posted 2008-05-11 16:16:41.

Boyfriend’s Test Spanking

The woman has begun to feel that the relationship with her boyfriend is getting serious. The time has come to see if the young male can accept the discipline she would enforce on any man that she married or lived with.


Taking him over her lap she begins a test hand spanking. If he responds properly she will give him a talk about gender roles and his place in any relationship with a dominant woman.

If he rebels against the spanking, she will no longer date him. She can’t waste time on an unacceptable man who does not know his place.

Sissymaid’s Punishment Spanking

Submissive Sissymaid’s Discipline

Punished Sissy Maid HunnyB
See more F/m sissy drawings by HunnyB.

I awake with a start. As I regain consciousness I become aware of my surroundings. I am in Mistress Megan’s bedroom, the evening sky darkening the room as the light fades. I am seated in a straight back chair, tightly bound to it with clothes line wrapped below my bust and around my waist. My hands are locked behind me in steel cuffs. My legs are tied together at the ankle and below the knee with lengths of nylon cut from Megan’s discarded stockings. More rope binds my shins to the bracing between the chair legs.

My legs feel sleek in my own nylon stockings, my torso hugged by the comfortable Lycra grip of a long-line bra. The bra cups are filled out by breast forms that stretched the material tight and pressed against my nipples, tender and sore from Megan’s clamps. My cheeks are sore also, throbbing dully under the girdle I wore beneath my lacy white slip.

I lick my lips and tasted the gloss upon them. I recall that I had applied lipstick and gloss as part of the makeup ritual Megan has taught me. My nostrils detect the light smoky scent of perfume, the one that Megan had purchased for me at Macy’s.

I glance up and see my blue and white waitress uniform on its hanger, the apron draped across the shoulder. I had worn this dress several hours today, from the time I came home from my job at the bank until about an hour or so ago when I was bound to the chair. I had worn my lingerie and nylon stockings all day at work. My suit pants covered my girdle and hose, its jacket concealing the bra which would be so visible through a white shirt. I wore socks over my stockings, but sometimes, if I wore dark stockings, I left the socks off and hoped the other girls at the bank didn’t notice my leg wear, visible between the hem of the pant leg and the top of the shoe was a little bit too shear for men’s socks!

Megan has me wear the waitress dress and apron as I perform my daily chores about the house, vacuuming the floors, scrubbing the tile and porcelain, washing windows, doing her laundry, ironing her blouses and skirts along with a hundred other chores to serve Her. Although some chores such as the dishes, laundry and cooking are done daily, each day of the week my chores are focused on a particular part of the house. Mondays were the bedrooms and hall; Tuesdays were the bathroom and laundry room. As today was Wednesday, I was assigned to clean the kitchen. Once I had washed all the dishes and counter surfaces, Megan had me on my knees, scrubbing the marble tiled floor until it shone.

To ensure a submissive disposition as I worked, Megan locks steel shackles with a short length of chain on my ankles and wrists. Although this shortens my stride and can make carrying things awkward, I never forget my place as I work. Megan also carry’s a riding crop with her to encourage my efforts should my energy slacken. When my chores for the day are complete, Megan has me bind myself to the chair in her bedroom. She used to tie the ropes and nylons around me herself, but later found it more convenient for me to tie myself up. Over the last year, I have become quiet skillful in self bondage. Once I have bound myself, She tests the tightness of the ropes, and woe unto me if there is slack in them! When she is satisfied with the rope-work, She will snap the cuffs on me and then leaves the room. She typically leaves me here for a couple of hours, ‘parked’ as She calls it, as She runs errands, talks to Her girlfriends on the phone, reads her mail or watches TV. She likes her time alone, with me safely tied up out of the way and not underfoot.

Sometimes she will leave the TV on for me to pass the time watching soap operas or a “chic flick” like Steel Magnolias. Megan calls this feminine education. She wants me to watch the girls in the film for insights into the correct mannerisms and comportment for a woman. She may also put on a Mozart CD for me to ‘enjoy’ while I wait her, but more on that later. When Megan’s mood is foul, Megan may tie a blind fold on me and/or duct tape my mouth shut.

The chair faces a full length mirror. As I pass my time in confinement, I have the opportunity to see myself in my current predicament. In my lingerie, makeup and styled hair, I see a young girl, bound and helpless. I must admit, the image I see does turn me on! Despite the helplessness of my current predicament and a feeling a bid of dread as I wait for the ordeal to come, I feel certain contentment as I awaited my Mistress. I feel a stirring between my legs that reminds me that I actually enjoy my position of servititude.

After a while though, my bondage becomes uncomfortable as the rope dig into my chest and waist. My arms become stiff from being pinned behind me and the tight heels on my feet pinch my feet as well. Yet I was in no real hurry for Megan to return. My pinched nipples and sore cheeks reminded me of the treatment I will experience upon Her return. Megan makes careful notes while I work, thoroughly noting the time it takes to complete each task and the degree of cleanliness of each surface and item to which I had attended. For every task that had taken longer than it’s budgeted time and for every chore not completed to Her level of satisfaction, I would have to answer for, submitting to Her whip, crop or paddle.

Glancing about the room, I see the various stations where I will be bound for the upcoming discipline session. Megan will vary the whipping ritual, as She likes to keep Her discipline sessions from becoming routine. Most often She will place my wrists in leather cuffs locked to chains hung from the gables of the dormer in her bedroom. Stripped down to my bra and panties, my back and buns are exposed to he crop, whip or cane. To keep me from moving around to much while being whipped, she’ll tie my legs together at the knee and ankle, linking the ankle bond to a hook in the floor.

Megan’s next favorite torture position is the footstool. On these occasions, she will have me kneel over her footstool, stripped again to the panties and bra with legs bound, and hands cuffed behind the back. She will place a leather collar around my neck and clip it to a hook on the stool to keep me in place while being lashed. When Megan is in a hurry, either pressed for time, or just too eager to administer pain, she’ll simply strip me and cuff my hands to the clothes bar in the closet. Sometimes she’ll also lock me in the closet for ‘parking’, and I can spend my time alone with her pretty dresses, and the scent of Her that they carry.

Today, Megan has ordained a heavy sentence of twenty lashes; three for taking an extra twelve minutes to complete scrubbing the kitchen floor, four for missing dust in the corner of a cabinet, three for neglecting to bow and curtsy as She passed, and most serious, ten for having a runner in my stockings, a serious misstep. Megan was so angry when she saw the tear! She scolded me for being so careless with my appearance and my clothing, which was, after all, a gift from her. She was also furious that I took over ten minutes to change into a new pair. I was tempted to reply that some of the ten minutes was taken up in undoing my ankle shackles to remove the pantyhose, but I have learned it is not wise to talk back to Her when I am being corrected! As it was, She assessed ten stokes with the riding crop summarily and another ten added to evening’s discipline session yet to come.

No matter how many strokes are assigned in the sentence however, Megan invariably adds many more. She takes great pleasure in administering discipline. The act of striking a man with a whip or cane causes an arousal in Her, and as Her slave, it is my role to cheerfully absorb this punishment for her pleasure.

I hear the clack of stiletto heels on the floor! My heart races as they near the bedroom. The door opens. There she stands before me in all her terrible beauty. “Hello, Cissy.” She greets me with a pat on the head, “Are you happy to see me Cissy?” She asks playfully.

“Yes, Mistress Megan.” I answer. “I am very happy to see you.”

“Well,” She’ll laugh as she fingers the whips and paddles on the rack on the wall, “We’ll see how happy you are in a few minutes!”

Megan has a ritual for which She uses to prepare herself to administer a whipping. First, she kicks off her shoes and shed her clothes, leaving them in the hamper for me to wash tomorrow. Then she dresses for the occasion.

Sometimes, Megan will have girlfriends over for a party, and the festivities may include a long drawn out discipline session with me or another slave as the sacrificial victim. Then, Megan and her friends may dress in leather miniskirts, bustiers, boots and other traditional dominatrice attire. However, for routine daily domestic discipline such as this evening, Megan prefers Victoria’s Secret type bedroom wear. She’ll put on some comfortable lingerie, like a teddy or silk night gown. Whatever She wears, she’ll top it off with a matching gauzy jacket, tied it at her waist. She has a few pairs of high heels she uses for these sessions, usually open back mules with a fuzzy tuft of cotton.

Seeing her so attired, I admire her beauty. The elegant features of her face, her flawless skin, golden hair, generous bosom, sleek waist and long legs make her the most beautiful woman I have ever seen. No man, I realize, could resist her demands, even if it means placing himself at her cruel mercies.

Megan completes her preparation with a spray of perfume, the special tangy one she uses only for these sessions. As the scent of it fills my nostrils, I am only too well reminded of the injury and pain I will shortly feel and am filled with a combination of horror and excitement as I realize once again what this charming, beautiful and evil woman has in store for me!

Megan un-cuffs me and has me untie the ropes fixing me to the chair. She has me shed my slip and bra, leaving me back exposed to feel her whip. She also instructs me to untie the nylons on my legs and to lose the pantyhose and girdle. Thus, my cheeks will also be a target for her paddle or cane.

Suspension is to be the order of the evening. Megan has me stand me upon a small wooden step and reach my arms up. She’ll places my wrists into leather cuffs and fix them to the chains hanging from the bolts in the ceiling. The step is then removed, and I hang by the wrists, able only to support myself by standing on my toes, but tonight Megan feels generous and she allows me to wear my heels.

She then binds my legs above the knee and at the ankle with Her nylons, and the ankle bond is tied to a hook in the floor. Megan doesn’t like to strike her whip at a ‘moving target’, and by fixing me legs in place She prevents me from moving around too much while I receive her beating. She finishes preparing me by fastening nipple clamps on me so I have something to think about while I await her. Sometimes if she’s angry (or not) she’ll put the blind fold and gag on me as well.

Megan then lights about a dozen candles around the room to set up a soft light. She places a CD in the player for background music. Her favorite is Mozart. I have received hundreds of lashes over the last two years all the while listening to the light and joyful tones of that wonderful composer!

With her slave ready to be beat and the mood set in the room, Megan sits for a moment to reflect before beginning the whipping. She is quite regal, seated in a large whicker chair, in her elegant gown, contentedly sipping her red wine. Then it begins:

“Tell me Cissy,” She asks. “Do you know why you are here?”

“I am here to please you and to serve you, Mistress Megan.” I meekly respond.

“And are you pleasing and serving me?” She’ll continue.

“Yes Mistress.” I answer. I am serving you to the best of my ability.”

“We’ll then.” She said, “We had better improve your abilities, because you are falling quite short in pleasing me!” She rises from her chair and approaches me. The terror in me rises with every step she takes.

She takes a leather glove from the rack and pulls it over her hand. She massages my buns for a few moments. The massage feels great and dulls the ache a little from last nights beating. Then she quickly changes tempo and deliver stinging slaps to each cheek. She then moves up my back to rub my shoulders and upper back for a few moments, tenderizing that area as well for the strikes they are to receive. Playfully, She fondles me though my panties until I am erect, which usually doesn’t take much work. For all her cruelty, Megan does want me to enjoy her whipping!

Tonight Megan will use two instruments, the paddle on me cheeks for the minor infractions and the whip across my back for the more serious matter of the runner in my pantyhose. She first takes the paddle, and standing behind me, swings it upward to the bottom of my buns. I am to count off each stroke, thanking her and asking for the next:


“Number One!” I count out, “Thank you Mistress Megan, May I have another?”


“Number Two! Thank you Mistress Megan, May I have another?”

The leather paddle stings my flesh at each blow. As the count gets higher, the pain becomes greater, and it is harder for me not to scream or moan in pain. But I have learned the hard way not to cry out while being whipped. Should I do so, Mistress Megan will simply gag me and double or triple the number of remaining lashes. She says she actually gets turned on listening to slaves moan through a gag while she whips them.

I hold up and receive only the prescribed number of ten blows from the paddle. Mistress Megan stops and rests for a moment. She is pleased with how well I held up during the beating and compliments me; “Good Girl, Cissy. You did well.” She rubs my panties to restore my erection and then sits for a moment to refill and sip her wine, resting before administering the final ordeal.

For my part, I stand in my heels, with my arms raised and chained to the ceiling, my nipples clamped in excruciating pain, my cheeks stinging and sore and hoping my strength will hold out for what is to come.

“I am very disappointed in you Cissy.” She says: “You know that nylon stockings require delicate handling when you put them on and while you are wearing them. You know it makes you look slutty to appear in them with runs!”

We have had this discussion many times before and I know that runs in my stockings are a major infraction to her. “You are supposed to be living as a woman now. You’re no longer just a little boy trying on his neighbors clothes!”

With that, She goes to the rack to select a heavier instrument of torture. She has a braided whip she occasionally uses when She is very displeased (like now). But as it cuts the flesh and leaves welts and scars, she will only use it on special occasions, like when she’s showing off for her friends. Tonight, Megan selects the leather strap. Although nearly as painful as the whip, the strap doesn’t cut the flesh. Thus, Mistress Megan has the feeling of power she gets from wielding a whip but without worrying too much about damaging me, her property.

Mistress Megan will strike the first blows lightly as she gets a feel for the distance and range of strap to the target. Then, when she has the feel of it, she will swing the strap with all her might, venting her anger over the torn stockings.

For my part, I’ll be counting off each stroke and vainly trying to hold off screaming my pain at the impact of each lash. From past experience, I doubt I’ll be able to hold up to ten lashes after standing on my toes for nearly an hour with my nipples clamped and taking ten or more swats of the paddle. If I’m lucky, I’ll stand up to the first five or six lashes before I scream and then receive the final eight or ten gagged as not to discomfort my Mistress with my screams.

Now the second part of the session begins!. I hang in the chains, legs secured together and nipples clamped. Mistress Megan comes up behind me with the strap. I’ll watch her every move through the full length mirror before me. I’ll see her raise her arm and bring the strap down upon me.

Swish! I hear the strap as it sails through the air and watch in the mirror as she strikes the blow.

Crack! I hear as it lands on my defenseless flesh and feel the sharp pain and sting of the leather on my flesh.

“One!” I count, “Thank You Mistress Megan. May I have the next?”



“Two! Thank You Mistress Megan. May I have the next?”



“Three! Thank You Mistress Megan. May I have the next?”



“Four! Thank You Mistress Megan. May I have the next?” Each stoke of the strap is harder than the last and my pain grows more and more.



“Five! Thank You Mistress Megan. May I have the next?” I start to weaken, but will use every ounce of strength not to scream out.



“Six! Thank You Mistress Megan. May I have the next?” By now, the pain is excruciating. I don’t know if I can take any more.



“Aahh, aagh!” I scream as the terrible strap bites my flesh one too many times for me to bear. “I mean Seven! Thank You Mistress Megan. May I have the next?” I plead, hoping she will take mercy on me.

“Did you just scream?” She asks indignantly.

“Yes, Mistress Megan,” I answer sheepishly.

“You will learn to take your punishment, you sissy!” She says sternly. With that she places a leather bit in my mouth and tie it around the back of my neck. Then she completes the sentence.



“Eight!” She continues the count as I moan into my gag.






“Ten!” The lashes come faster and harder as Megan becomes more aroused.







Just one more to go! I can almost feel the end of the ordeal.




‘Is it over?’ I wonder.



“Fourteen!” and then;




Swish! Crack!

“Sixteen!” Mistress is now too aroused to stop herself. She keeps swing the strap, harder and faster. All I can do is to cry out softly through the gag. There is no stopping her now!



“Seventeen.” My strength breaks. My knees give out as I hang limply in the chains.

“Damn it,” She yells, “Don’t you move while I’m whipping you!”

I buck up and stand, knees locked.






“Nineteen!” The last two are softer. Mistress must be tiring. There is hope for me at last!



“Twenty!” This was the hardest yet! It must be her grand finale!


Crack! “Twenty-One!” This one was light. My Mistress’s energy is spent. Perhaps now she’ll have pity on me and release me from my chains.

Mistress Megan replaces the strap and paddle on the rack and retreats to her wicker throne. I know now the whipping is over. She softly catches her breath and sips her wine while I still dangle in my chains. I catch my breath, my nostril flaring as I am still gagged. I promise myself that I will never appear again before my Mistress in torn pantyhose. The consequences are just too painful!

Megan stands and approaches the rack. She picks up the rattan cane and I realize to my horror that there is more to come! She removes the leather bit that I may speak.

“Do you love me Cissy?” She asks.

“Yes, Mistress Megan,” I answer. When a woman has me naked and chained and is ready to beat me, I have learned to do or say anything that might keep me on her good side! “I love you with all my heart.” I added for affect.

“Do you live to serve me?” She asks.

“Yes, Mistress, I will serve you always in any way you desire.”

Megan flicks the cane, “It pleases me to beat you, Cissy.” She says. I am only too aware of this, but I say nothing. “Will you cheerfully submit to be beaten? May I strike you with the cane?”

“Yes, Mistress,” I answer, “Please strike me with the cane.” Again, I am in no real position to negotiate here.

“Thank You, Cissy.” She replies. “How many strokes would you like?”

Now here’s a trick question. None would be my first choice, two or three I might be able to handle, four or more would be too much as I am still debilitated from the first two beatings I have received this evening. However, if I only ask for a one or two, Megan will be disappointed and may become angry. I sure don’t want Mistress Megan to become disappointed or angry right now.

“Please strike me three times with the cane, Mistress Megan.” I request. I don’t know if I can handle more than three cuts, so I decide not to gamble.

“Three?” She asks coyly, “Is that all, Cissy?”

“Oh, Mistress Megan…” I stammer, “Please strike me four times.” Three or four, what’s the difference, I wonder.

“Very Well, slave. Four lashes it will be.” Megan happily agrees.

I grit my teeth as I watch in the mirror as she approaches with the cane.



“Ooow!” I scream. The sudden shot of pain as the rattan bites into the soft flesh of the underside of my butt completely takes my breath away and buckles my knees.

“One!” Megan says proudly.



“Ooow!” I scream again, tears running down my face.

“Two!” Mistress Megan calls out. “If you’re going to scream dear, don’t be so loud or you’ll wake the neighbors!” she says playfully. I don’t even bother to try to stand straight, but just dangle in my chains sobbing.




“Oooh..” I moan weakly.



“Four!” Mistress says proudly.

“Please, Mistress,” I sob softly, “No more, please!”

“No more, Cissy.” Megan says. She un-cuffs my wrists and I settle on the floor. “At least, no more for tonight!”

I sit on the floor and untie my legs. My shoulders and butt are throbbing in pain from the sting of the thirty five blows they have received from Megan’s crop, paddle, strap and cane. I am a wreck, sobbing in pain, sweat and humiliation.

Megan takes a tube of ointment and rubs some into the welts on my shoulder. She gently massages the gel onto my beaten flesh and the pain slowly ebbs. “You’re a good girl, Cissy.” She coos, “You have served your Mistress well tonight. I am proud of you.”

Her assurance that my sacrifice has been appreciated helps to ease my pain. After about ten minutes my sobs and tears have stopped, and the sharp pain has ebbed into dull aches. I feel a little normal again after two hours of bondage and beatings.

“Go take a shower and clean yourself up.” Megan instructs, “And fix your makeup.”

I nod and head to the bathroom. I take a quick shower, wash my face and hair and quickly towel off. Mistress wants me back in her bedroom quickly, so I only reapply my lipstick. There is no time for foundation, blush, eye shadow or blush. Besides, Megan is really only interested in my lips at this point.

I return to the bedroom wearing only panties, a slip and lipstick. The welts on my back and thighs rule out a bra or pantyhose. Mistress has me sit on the edge of the bed and retie the nylons around my knees and ankles. She then binds my hands behind my back, but with soft nylons now and not cold steel cuffs.

With me safely and comfortably secured, she rubs the front of my panties until I am once again erect. She places her hand inside my panties and rubs my erection until it is as hard as it can get. She then rolls a condom over it and pulls the panty back over it. The condom is the resoivior style and will catch my fluid and not leave any stains behind on Mistress Megan’s bed.

Lastly, she ties a silk scarf over my eyes. Mistress Megan will soon be unsnapping the bottom of her teddy, and that is a sight she does not permit her slaves to see.

“Come to me!” Megan orders.

I roll onto the bed and wriggle around until I am between her legs, my lips next to her Womanhood. Megan pushes my head down between her legs and I go to work. My tongue licks follows the lines of her slit until I find her clitoris. Then I really go to work and soon it is Megan’s turn to moan! I work my tongue on her until she climaxes with a shriek.

Now I can work on my own needs. I continue to flick my tongue in and out of my Mistresses moist slit while gently lifting and lowering my hips against the mattress. I sense the softness of the slip and panties against my tender skin, the ache of the beaten muscles in my back and butt, and the helplessness of the nylon bindings on my legs and wrists. All these sensations stimulate me and I continue to service my Mistress. Despite all the sensations I have experienced this evening and how stimulated they made me, it is the taste of my Mistresses’ pussy and it scent that sends me over the edge. I control my release until Megan is ready to come again and we climax together.

“Oh, Cissy!”, Mistress says as she rolls me away from her. We lay there quietly for a moment and then I hear her snap her teddy. “That was perfect! Good Girl.” She gives me a pat on the head and unties my hands. I remove the blindfold and nylons from my legs.

As I stand to leave, Megan gives me a quick peck on the cheek. “That will be all for this evening.” She says, “You are dismissed.”

“Good Night, Mistress.” I say with a slight curtsy of my slip. I gather up my clothes and tip-toe to the door. I softly close the door behind me as leave my Mistress. I am tired, sore, happy and fulfilled. I can’t wait for tomorrow!

The Shrimp

As someone with a tiny penis (1.9” soft & 3.25” hard), I was very interested to read people’s comments on small penis humiliation, and thought I would add my 50 cents worth. In spite of having a bit of a hang-up about being underendowed, I can’t deny that I do get secretly turned on when people laugh at my size.

It all started in my school days, when I was dating a girl called Louise, who was a few years younger than me and who was my first proper girlfriend. As a joke, a couple of my so-called friends sent her a love letter, which they pretended was from me. I never saw it myself, so I don’t know exactly what was in it, but I gather it went into explicit detail about my cock size (damn those communal showers).

Louise must have known it wasn’t really from me, but rather than being shocked, it seems she was curious about it. So the next time we were alone together in her bedroom, she began unbuttoning my jeans. I knew nothing about the letter, of course, so I thought she was getting fresh with me, because she wanted to take our relationship to the next level (we had only ever kissed before). This was like a dream come true to me at the time, because I was somewhat wet behind the ears and didn’t realise how truly tiny my cock was.

Louise, it turned out, was not at all wet behind the ears. No sooner had she pulled out my throbbing cock than she burst into laughter and told me that her 7-year old brother was bigger than me. Whereupon, my cock shrivelled up even smaller than normal and I shoved it back in my pants, my face crimson with embarrassment.

She finished with me right then and there. Not only that, but the next day she told all her friends at school, and they told their friends and so on, and so on. The upshot was I spent the rest of my school life being called the Shrimp.

There were various other incidents over the years where my cock ended up being laughed at, which I won’t go into here. The upshot is I ended up being more than a little reluctant to let girls go anywhere near it until I was very comfortable with them. Then, slowly I realised that I had come to like it when people told me I was small… it turned me on.

Originally posted 2008-02-22 13:00:08.