Sissy Learns the Difference
Bdsm Story

Sissy Learns the Difference

by Pinphillip 17 min read 4.3 (10,600 views)
femdom cucoldry humiliation maledom fmm sissy maid sissy cbt
🎧

Audio Narration

Audio not available
Audio narration not available for this story

Richard finds this Femdom couple intriguing and arousing. And individually, each fascinates him.

Mistress Hayley is self-assured, disarmingly charming, light-hearted and well-balanced. She attracts attention, respect, and affection. Her innate modesty only cements this. She is a medical professional, possessed of a certain precision and self-discipline that hones her sexual power and erotic dominance.

Her sissy slave is often oafish. Yet also sweet, devoted, and sincere. Beyond its deficiencies, the slave is creative, talented, and hardworking. Of its physical attributes, it is often complimented for having shapely legs.

In its private life, Ms. Hayley's slave is regularly referred to as "it," "bitch," or "Her bitch." It bears a tattooed script on its hairless pubic mound that literally says, "Her bitch." Most of their friends know the nature of their relationship.

Though she is typically discreet, she does enjoy humiliating her toy in front of others: either overtly or covertly.

Covertly, she sometimes requires that it wear ugly, ill fitting, awkward or inappropriate clothing in public such that others can get a hint of its inferiority that way. Everyone needn't know the full extent of her slave's subservience. Its "forced" humiliation in public is still a pleasure for her to observe. This while she is a seemingly innocent bystander. She may even pretend not to know the hapless wimp.

Even at a social distance, Ms. Hayley's graciousness thrills her slave to no end, especially when she gives it ways to suffer for her.

Mistress and slave are deeply in love and well-matched. They have lived together for years and were recently married. There is a fathomless well of trust between them. Her presence never fails to make her slave's heart sing. And it is a near constant source of amusement for her. Though her fortunate cruelties factor heavily, the two are mutually supportive and very affectionate with one another.

Richard can see the symbiosis between Mistress and slave. And he enjoys how deliciously wicked their Superior/inferior reality is.

Richard most enjoys her intellect, the sound of her voice, and her mature and natural beauty.

He is intrigued by her dominance. But, he is inclined to meet her on a power-neutral basis with a somewhat vanilla sexual connection. With things leaning towards soft Femdom, if there is any power exchange between them.

"Somewhat vanilla" except in that the emasculation of her sissy supercharges his own manhood, while acting as a perverse aphrodisiac for both Richard and Mistress Hayley.

She isn't a Switch, but he is. She isn't bisexual but he is.

He is most attracted to women in a gentlemanly manner. But he adores tormenting the sissy for her amusement as they egg each other on.

There is something about her bitch that initiates sadistic license and free rein. Its obedience and responsiveness are assured. It knows that it needs to suffer and to serve. Otherwise, being compulsively masochistic, it would likely be fucking up (even more than it already does) just to subconsciously arrive at some form of discomfort in its life.

Few of the submissive women that Richard has known are as much of a pain and humiliation slut as her slave. Despite being a Switch himself, he has never regarded women as being so appropriately degradable as the sissy that Mistress Hayley owns.

The three met at a BDSM event. Her bitch immediately felt at ease around him though it was quickly sidelined in the conversation.

It enjoyed kneeling quietly at her heel as she snapped her fingers and pointed to the ground there. The slave took up position accordingly, while she and Richard got to know one another.

It knelt with legs spread, hands behind its back, eyes focused on the ground a few feet in front. They spoke for a good 30 minutes or so as they stood there occasionally greeting others more briefly. The typically gregarious sissy was not acknowledged by anyone who greeted the two peers.

Mistress Hayley is usually the one who attracts attention and acknowledgment, regardless of who she is with. She made it a point to introduce Richard to the others she already knew.

She became most animated with him, in discussing various absurdities and ironies that she had run across. Or clueing him in on her non-kink hobbies and interests. While he was more gently being quizzed by her about his own life, interests, career, and so forth.

Richard is handsome, well dressed, ex-military, and also works in health care. Loves gardening and appreciates the fine and performing arts. He is easygoing, outgoing, intellectually gifted and curious, and discreetly kinky as fuck.

Her bitch noticed a good rhythm and balance to their conversation and the topics upon which it dwelt. That reminded it of its first encounters with her. Just as she was gathering an affectional familiarity with him, so was her sissy by extension. Her bitch thought him classy and worthy of her trust. That he is respectful of its Goddess and not acting like a self-absorbed 'Domly Dom'. Knowing if he were, she probably wouldn't still be conversing with him.

As they had been speaking, Ms. Hayley noticed Richard looking amusedly at the sissy at her heel. So, she pulled the chain on its slave collar and snapped her fingers again.

This time pointing her slave to Richard's shoes, she said to Richard: "This is my little bitch in a cage. Your shoes look a bit dusty. Would you like it to lick them clean for you?"

"Hah. But of course, why don't we retire to the couch over there so it can also clean the soles?" he said.

"Great idea! First, let's have it fetch some refreshments. I'll have some coffee and a cookie. Would you like something?"

"A coffee for me too," he said.

Off the sissy scurried in its heels, corset, hose, and translucent micro-mini skirt. Anyone at the party could see through the skirt that its 'little problem' was respectfully chaste and presentable in its pink micro-chastity cage. And also, that it was sporting a large anal dildo held in by a leather harness.

When asked about that she said, "I've been taking it steadily smaller on the cage, and larger on the rubber cock in its boi pussy. Wonderful attitude adjustment for the sissy."

Returning within a couple of minutes, her bitch served the refreshments and silently set about cleaning Richard's shoes with its tongue while they spoke as if it weren't there.

With another snap of her fingers, she said, "Now mine, loser".

Then it quickly swallowed the dirt and grit in its dry mouth and blissfully set about worshiping and cleaning its gorgeous owner's boots in turn: glancing to see the ravenously cruel look on Richard's face and the growing bulge in his jeans.

"Enough," she said as she waved the boot licker off a short while later.

She was quite the conversationalist with Richard, however. Shifting back and forth from a perversely conspiratorial tone to a lilting and relaxed connection. They were clearly, hitting it off.

Her bitch listened attentively, if invisibly, to its betters. Richard has the social grace to reciprocate conversationally, which is an unfortunately rare quality in some circles.

Still kneeling with eyes involuntarily fixed upon their shoes, the sissy was trying not to obtrusively stare at its beautiful Goddess or her handsome new friend.

A good menial waits to be of use.

Such an impression was made between Ms. Hayley and her new male peer that a private dinner engagement was arranged on the spot. And the two continued to communicate online thereafter.

An impromptu dinner-out between just the two of them also took place prior to the private dinner at home. For which her bitch offered its credit card to spare any expense that might be involved. Mistress mentioned that she had some plans to make with Richard, for their private dinner soon thereafter.

It was a lengthy date including an early dinner out. Her sissy maid happily did its cleaning chores while its betters were out enjoying themselves. It was required to message photo documentation of itself cleaning each of the toilets while semi-naked and caged. It imagined that she wanted to share the pics with her newfound friend and this was later confirmed.

Mistress Hayley is also a superior chef. So, when the private dinner date arrived, it was she who had cooked. But her sissy maid was appointed to serve the meal.

It was muffled with a gag which featured a penis-shaped silicon insert to stuff its throat while it was serving. But the gag was buckled in a bit loose so that the sissy could manage to swallow its saliva while working, rather than drooling all over the place. It was similarly outfitted to its recent presentation when they had all met, but with a skimpy maid's dress this time.

The dinner table was set for two. As Mistress Hayley and Richard settled in to enjoy the main course, the sissy was instructed to remove its penis-shaped muzzle and to practice deep throating with a larger 8" dildo, with no audible gagging on its part. Mistress did not like the sound of it gagging or retching. This while on its knees in the adjacent kitchen. Best to do that on an empty stomach anyway. Mistress often has it do this during dinner. She calls it "the cocksucker diet."

She was keen on her bitch taking cock in both of its holes. In part, because being penetrated while forbidden penetration on its own part, made its emasculation and long-term denial all the more impactful. And because its "sex life" was appropriately shifted from active to passive thereby. When it thinks of "sex" it never thinks of fucking or being sucked. But rather, it thinks of having to lick, suck or get fucked while being used like the masochist and inferior that it is. Its focus being the pleasure of its Owner and her peers and not its own. Including any rare occasion when its Mistress might wish to make use of the diminutive "penis" that she owns.

She requires the metaphorical castration of her dicklet carrier. While keeping the dicklet in near constant aching need. This is a form of contrition for the bitch, for its past pretense and privilege. Marking the fact that its faux masculinity has been permanently revoked.

Richard and Hayley's main course at dinner having been served and with a bottle of wine chilling on the table, their conversation rambled along cordially, this time for closer to an hour.

Now and then, if the sissy made the slightest noise as it was throat training in the kitchen, they would just pause, whisper and snicker to one another. Each time they paused their conversation; her bitch was afraid that they would be displeased and angry that it was throating too noisily. But they just found the sounds of its training entertaining.

As it had served their dessert, the slave was instructed to join its Superiors at the table while they finished dinner. It still wasn't allowed to eat anything. As is the custom, not until its full service and cleaning are done might it have leftovers (sometimes from a dish on the floor).

Being hungry and impossibly horny, her bitch was almost drooling from both ends. It was about six weeks out from its last prostate milking and supervised ruin but knew better than to mention it. Mention was made of the tell-tale wet spot on its lace panties from the slave leaking pre-cum ("sissy tears"). Richard suggested requiring that the sissy use panty liners while Ms. Hayley told him that it always had to lick up any of its little dribbles anyway.

The conversation over dessert consisted primarily of the bitch answering Richard's questions about itself. Some semi-normative bonding did take place between Richard and the sissy slave, which helped put everyone further at ease.

As they shifted from the dining to the living room things took a turn. Her bitch was instructed to kneel at their feet facing the couch as they kissed passionately for a couple of minutes.

"Now faggot, there is something that I know that you'd love to see." She whispered something to Richard. Then he stood up and undid his pants, which slid down his toned and naturally hairless legs revealing his already erect cock. Richard's skin being as hairless as her sissy was much to Ms. Hayley's liking.

"That's right sissy, get a good look at an actual man's cock. Isn't it beautiful?"

Her bitch knew that it was. It wasn't as small as the sissy's 'clitty' but it wasn't much larger than normal either. It was circumcised, perfectly proportioned for her, and hard as a rock.

"Yes, Ms. Hayley, Richard's cock is beautiful." the dickless sissy whispered.

"And what's more, it's attached to an actual man. Now watch and learn," she said.

"But first remind me, when was the last time that you felt these lips on that little defect of yours? And how long did that last before you were locked back up without any release?"

"It was about 12 months ago, Goddess, and it lasted for about 30 seconds," the sissy admitted.

"And you're on the outside edge of the longest you've ever been denied any sort of release. And like a good loser, you have not complained or hinted around or pushed for anything except to thank your Owner for keeping you respectfully chaste and denied. Just look at you. Fortunately, no one will ever mistake you for the man of any house, ever again."

Roughly stroking Richard's raging cock, she paused her matter-of-fact commentary, to knowingly observe her slave's pointless ego quietly imploding. They could also see that nothing turned the sissy on more than being treated in just this way.

"You know that we enjoy your aching and straining: when your little sissy parts are screaming in vain for any sort of relief. Because that is exactly as it should be. And that is definitely one of the best ways that you can please us. Your suffering is as delightful as your obedience. And the fact that you can't seem to disobey no matter what you think or feel in the moment, proves that this is what you need most of all."

It has repeated that phrase, "exactly as it should be", many times to itself at the limits of its masochistic tolerances. When it might otherwise panic or balk at its necessary training and conditioning. This always helps it to focus and obey. She had given it that framework early on and reinforced it through hypno-loops and having it recite it back to Her and to itself as a mantra, countless times.

"So desperately horny, huh? It mustn't think that it could ever 'deserve' to cum. All that my sissy needs is a big cock in its boi pussy, causing it to cry sissy tears of joy, while still caged. Get used to that ache, for the rest of your life, bitch."

As it was being so instructed, it let out a little sigh of surrender. Its eyes glazed over as it entered a triggered, subservient trance, and its mental conditioning kicked into gear.

She could see that her words now entered its soul and took its mind and heart completely. Her speech had a ritualistic cadence and rhythm like the hypnogogic casting of a spell. To her slave, her voice sounded like it was coming from far away, yet so deep inside its mind as well.

"That little problem of yours isn't an actual man's cock at all. It's a mere training appendage: for me to tease, torment and use you like the filthy little bitch that you are."

Her words were then indelibly formative for the suggestible and malleable subservient.

"You will watch closely as our handsome friend takes his pleasure. Oh, and while you look on, you will paddle those little blueberries for our amusement!"

"Yummy! Yeah, that's it. Fold your little skirt up on your torso. Spread those sissy smooth legs and thrust out your hips to present them. Those tiny balls must be aching so very much by now. I'll bet that the paddling will feel almost like a relief. Precisely the kind of 'relief' that a torture toy deserves."

Her voice was dripping with contempt as her bitch whimpered and the two Superiors laughed heartily.

"Well, if you don't need and want every bit of this, why is that little nubbin straining so and why is it crying 'sissy tears' right now? You LOVE it, bitch. That's why."

"In fact, you will BEG him ever so urgently to please let you paddle those aching blue balls like the stupid little sissy that you are, while he takes his full, complete, and satisfying orgasm at your expense."

They were dying laughing as the sissy sincerely and pleadingly begged to suffer accordingly. In stark contrast to the utmost pleasure of its Superior. In the highest-pitched and meekest tone of voice imaginable.

To which Richard quickly agreed: "Oh absolutely, cuck, that should be instructive for you."

With that, she stepped up the stroking of Richard's cock. Then their eyes met as she deftly took him in her mouth. He was breathing deeply and relishing her oral expertise. Either her hand or her mouth or both were then all over his manhood non-stop.

As its betters got busy, the sissy slave took the vinyl-covered ruler type device from the coffee table and began to slap itself. After several minutes, their attention briefly returned to the slave.

"HARDER, sissy. That's it. You need to feel it up in your abdomen. As he nears his climax in my luscious mouth, I want you to be slapping those peanuts as hard as you possibly can. Got it?"

"Yes, my Superior".

"Such a good gurl."

They both laughed derisively again at the grunting masochist at their feet. Its torment, stoking their lust.

"See the difference now? Between you and an actual man? Tell me. How long is the rubber training cock inside you right now?"

"About 12 inches, my Superior."

"And how long is that pink plastic corrective piece of your anatomy?" She said while pointing to its pink micro-cage.

"About an inch long, Mistress."

"Sounds like an appropriate ratio to me," he chuckled, while breathlessly approaching his manly pleasure.

When she wasn't sensually caressing Richard's magnificent cock with her mouth, the pale plum-colored mushroom head was observable at maximum swell and the shaft was slightly curved but thrust straight up and out. She had also begun to please her sex with a glistening finger or two.

Meanwhile, the plastic-capped irrelevance of her sissy was straining painfully in its appropriate housing. The slender pink leather anti-fall strap that held the cage close to the sissy's hips was stretched out like the ropes of a tent, which was staked to the ground. As the dicklet was hopelessly attempting to get fully erect.

Evidently from its responses, her slave did love every bit of this. Which registered with its betters as all the more pathetic.

Richard's thighs stiffened, and his member was close to erupting. He sat down next to her to steady himself as she had him on edge and wanted him to fully enjoy his orgasm. He was almost growling with lust. She was cooing and encouraging him when not avidly sucking him off.

He didn't finish in her lovely mouth though. She caught most of his huge load in her slender hand. With her other hand she snapped her fingers again and pointed at the floor. The sissy knew that it must scramble to lick up the ejaculate that had overflowed from her hand and dribbled onto the floor.

"There ya go, piglet. See. We weren't going to let you go hungry. Now look at the tasty protein treat I have for you here. Get your suck hole wide open like a baby bird," as she dumped the snowball into its waiting mouth.

As it also then licked and sucked her fingers clean of Richard's cum, he already started getting hard again. He was further aroused by how focused the finger-sucking sissy was. How it clearly couldn't wait to suck dick.

"Now you'll fluff him, cock sucker."

Her sissy had been trained to please her male peers. Trained not just to suck cock but to worship it, as a good gurl should.

By this time, she had readied herself for some dick and as luck (and suck) would have it, Richard was fully hard again. It wasn't more than about 20 minutes before they were both cumming in unison.

Enjoyed this story?

Rate it and discover more like it

You Might Also Like