Category: Mr. S

#3032 – Sissy Story 73 – Do You Need a Sissy Spanking?

It’s been months since the last time I posted a sissy story!
It’s time for a new one :)
So you sissies got something to read this weekend :)
Mr. S returns with another exclusive story for our site!
His short stories from a master’s perspective are always exciting to read ;)
And this one goes out specially for you spanking-loving sissy sluts :)


Do You Need a Sissy Spanking?

by Mr. S

I love spankings in all forms. The submission alone is great. A sissy, bent over, helpless in front of me makes me revel in my dominance. Knowing that I can make her feel pleasure and pain simultaneously drives me wild.

We meet at the heavy leather bondage table and I immediately have you strip down to your delicate side tied white thong. You climb on to the table on all fours and I fasten your wrists and ankles to the corners of the table loosely. I want lots of play in your bondage so you can wriggle and fight as I spank. Just enough restraint to keep your legs a little spread and down on all fours.

After giving you a moment to get comfortable and relaxed, I make contact, gently bringing my hands up your outer thighs. At the top, I bring my hands around and cup your tucked sissy clit. You whimper and arch back, showing you’re good and horny. Lightly I trace your panty line back over your hips, tickling you and getting you to giggle and shake. Once back to the apex of your thong I let my hands slide down your ass and onto your inner thighs. Your heavy breathing tells me all I need to know that you’re enjoying everything.

I bring my hands back up to your ass and give it a good squeeze. Repeatedly I pull your ass apart and squeeze it together. I love how your little white thong appears and disappears in your big, hormone induced bubble butt. I keep kneading and moving your ass.

Then it happens. I give you the first light smack on your ass. Very gentle, very easy. Just enough to get your back to pop up a little in surprise. My left hand slides down your ass and presses up gently on your pantied clit delicately holding you in a perfect position as I softly spank with my right hand. Over and over my hand falls on your ass covering every inch with the lightest of smacks to warm you up.

Soon you’re whimpering and crooning and I know it’s time to mix up my style. With more force I use both hands randomly switching where and how I spank. You lose the ability to predict how you will be hit and it heightens the experience. I’m using just enough force for you to feel a little pain and this along with the random location gets you jumping and bobbing a little bit.

I return to rubbing your slightly pink butt and rubbing your panty crotch. You drop your head to rest and to give me better access. Time to go a little deeper. Gently I untie the sides of your thong and pull it off of you. It ratchets up your horniness to have your clit out but also gives a little shame not having this barest of security blankets. Back to rubbing. Slow kneading and a few firm sharp smacks. Eventually I grab firm hold of your clit in one hand and spank with the other, cruelly using your sex to draw you back into each spank.

I break from you for a few moments and you hesitate nervously not knowing what to do. You’d been rhythmically swaying but without my smacks to guide your movements you slow and stop. You know not to speak or look back during a spanking but overcome with curiosity you turn your head ever so slightly to get a view of what’s coming. I catch your violation and immediately correct it. I roughly buckle a ballgag in your mouth tightly. It has a ring coming out of it which I clip to the table forcing you to keep your face down to the table. As I circle back around I give you two hard spanks on each ass cheek causing you to lurch and tug at the gag holding you face down. You worry the fun spanking has just turned punishment.

The next sensation hits you like a freight train. You shudder and squirm as I slap a handful of coconut oil in your ass crack. It begins liquefying on contact and I smear it around, making a ring around your ass pussy and then spread it out over your ass. Your big ass now glistens and I keep rubbing all over your swollen achy sissy balls. I notice the first drop of precum swelling on the tip of your clit. I stop, put a condom on you to catch your spills, and slap another glob of coconut oil into your ass crack.

You begin to ponder the point of the oil. From your position you can’t see your beautiful shiny ass but the delicate aroma of coconut is pleasant and it does seem to provide some lubrication. You’re jarred back to reality as I spank you hard. You lurch, tugging at your gag and let out a muffled sound. Over what feels like an eternity I rain firm, hard spanks over your ass which is now a shiny crimson delight. You yelp and squirm and struggle but of all your restraints it’s that cruel ballgag that holds you most uncomfortably. By now you’re tearing up and drooling uncontrollably and I ease back, gently rubbing your slippery ass and tugging your clit to keep you in a horny mood.

As soon as I feel you relax I give two quick smacks and then slowly work my index finger around your ass pussy. You purr behind the gag and I gently slip my finger in. Slowly I rub the oil around lubing you up. With my other hand I gently tug your balls to keep you arched like I want. Once again you’re lost to the world as you ride my probing finger and once again I drag you back by releasing your balls and smacking your ass.

As you buck from the impact you realize the challenge you face. Your muscles want to tighten with each spank but you must also try to keep your ass relaxed as I finger it. As I spank you more and more I feel your fuckhole clamp down on my finger as each smack hits home. Your ass is very bright red and I can tell it’s painful. I get great pleasure watching you fight your body’s impulses both to keep your ass open and not jerk your head around the secured gag.

You’re sweating hard and crying with drool gurgling whimpers from your gagged mouth so I ease up and take out my finger. With one hand I cradle your condom encased clit pointing it straight back from you. With the other hand I gingerly spank your clit, just under the tip, where it’s so sensitive. I increase force over time and soon you’re back to fighting me. I love it because I’ve got a hold of you and despite your squirming protests I can see the condom slowly filling with your juice.

Eventually I release your clit and go back to your ass. Now I slide in my middle and ring fingers. The spanking starts again and once more you’re fighting your body. It’s a thing of beauty to manhandle your big shiny crimson ass and keep you squirming in a mix of pleasure and pain. You bite hard on the ballgag for relief and look at the puddles of tears and drool beneath your face, fighting to continue.

I sense that you’re near a climax so I push my fingers deep inside to hit that “sissy spot” and simultaneously push my thumb underneath and rub right behind your sissy balls. I hold you like a bowling ball and work your inner pussy from both sides. As I hit the spot the spanking gets furious and soon you’re bucking like a bull uncontrollable in the throes of sensation. I hear muffled screams and gasping breaths as I work your sex with my hand. I time each smack to disrupt and confuse you. As you try to get a calming breath I smack your ass to stop it.

As you lose control of your body and fall into an orgasmic bliss I keep pumping until you are well past finished, drawing out your anal orgasm. The spanking stops and I slowly withdraw my fingers. You’re exhausted and covered in sweat now sucking deep breaths to calm down. I remove your condom, tie a knot around it to keep the milk in and drop it under your face. You marvel at how much goo oozed out and then begin to wonder what I intend to do with it. That idea fades quickly as you for the first time notice how burning and sore your ass is. You begin to wonder if you’ll be able to sit tomorrow…


It’s been a while since the last story by Mister S!
So here is a new hot short story!
As always, it’s so exciting to read something from Mister’s POV ;)
Enjoy gurls!

A Little Help For the First Time

by Mr. S

It’s so hard to meet a good sissy these days. Oh sure everyone wants to chat online about fantasies but to find one willing to do my online training and then even show up… Wow, that’s a real gem.

You arrive at my house as instructed and ring the bell. Almost immediately the door opens and you are greeted by a lady in a robe who beckons you in.

“You must be Sissy Lilly. You may call me Sissy Daisy.”

As your eyes adjust you get a better look at Daisy. Sure enough, this pretty girl is really a boy. She takes your coat and guides you to the back of the house into a spacious bathroom sparkling with white tile.

“Strip down and hop in,” she says as she gestures to the bathtub which is frothing with bubbles and flower petals. “Oh, don’t be shy. I’ve seen all the pictures you’ve sent to Sir.” With that encouragement you slowly strip naked and get into the tub. “Relax for a bit,” Daisy tells you as she scoops up your clothes and scampers out of the bathroom.

At first you panic as you’ve lost your clothing but you realize you wouldn’t catch her anyway. Instead you lie back and try to relax. It gets easier as the warm bath, bubbles, and delicate floral scent envelop your senses. The experience is very calming. Just as you’ve zoned out, Daisy returns and she kneels by the tub. She grabs a sponge and starts washing you down. It’s so relaxing as she gently cleans your body. Eventually she prompts you to stand and you do. She inspects you from head to toe.

“Oh, sweetie. You did a good job shaving. Sir will be so happy. Sit back down and soak and I’ll get your outfit together.” You relax in the tub and she scurries about getting everything together.

Eventually she directs you out of the tub and dries you with big fluffy warm towels. Once dry she helps you into a robe like hers and sits you by the mirror. From toe to head she grooms you. Starting with red nails and ending with a dark wig. She perfectly applies makeup and lipstick giving you dark eyes to match the wig and bright lips to match your nails.

At this point she helps you out of your robe. You’re a little shy still but finding it easier to be naked in front of her. She tosses the robe in a hamper and returns with a small box.

“You know about the chastity requirement, right?” She asks.

“Y-yes, he told me,” comes your slow, meek reply.

“Ever wear one of these before?” She follows up.

“No, no I haven’t,” you reply with nerves obvious in your voice.

“Well I think you’ll love it.” With that she kneels and slides the ring on immediately followed by the plastic tube which she wiggles on easily. Once the two are connected she threads the lock in place to hold it together.

“Where’s the key?” you ask.

“I don’t know. I’m sure he has it somewhere safe. Any pinching or tightness?” She rolls the cage around in her hands.

“No, not at all.”

“Good.” She rapidly clicks the lock shut. She rolls your encased package in her hands a bit more before returning to her feet. It’s oddly erotic letting her play with you while in chastity. She gets your outfit from the closet and returns.

“First things first.” She hands you a pair of panties and you step into them. They’re white, lacey, and most noticeably crotchless. As you pull them up your chastity cage flops out of them hiding nothing. As you tug them up you feel the delicate ruffles on the back. “Arms out.” Obediently you put your arms out and she threads a bra on you. It too is white and lacey. It’s a little tight and you stiffen your posture as Daisy slides behind you to fasten it. This done she hand you a skirt, a bright pink tartan skirt to put on. Pulling it up you realize it’s only about 4 inches long and won’t cover a thing. You do your best to position it on your hips but the comical shortness makes it useless. Daisy doesn’t skip a beat and fetches a pair of black four inch heels that she helps you into before popping back up.

“Well, what do you think?” she asks.

“I look ridiculous. I look like every teen boy’s fantasy of a schoolgirl.” You reply as you gaze into the mirror.

“I think you look sexy. And what better outfit for your first blowjob than a cute schoolgirl? Come with me.”

She leads you a few doors down the hall and into a large bedroom with a vaulted ceiling and Japanese inspired furniture. The bed sits low and the nightstands have bright potted orchids on them. It’s evidence of an analytical personality. You turn back to Daisy and stop in your tracks.

She’s removed her robe and to your surprise is dressed exactly like you. The bra, skirt, and panties are identical. She’s even got a chastity cage on just like yours. The only difference between you is your long dark brunette hair and her light blonde bob.

“Just relax, I’m here to help,” she says as she moves toward you. She puts her hands on your face and pulls you in kissing you gently. You panic and turn causing your chastity cage to clack against hers. “See, we can’t get in real trouble. Why don’t you relax and play with me? Sir will be along shortly.”

With that she pulls you back to her and begins kissing you passionately. You melt and fall into her arms returning her lustful embrace. The kissing deepens and she pushes you back until you fall onto the bed. She quickly kneels between your legs, grabbing your chastity lock in one hand and petting your encased sissy clit with the other.

“Aren’t these just great? You get turned on and expand only to be squeezed back. Even the squeeze is erotic. In fact it feels like you’ve grown as much as it will allow. Is it squeezing?”

“Yes but it’s not bad. A dull ache. Somehow I’m more aware. More horny…”

“I know. It’s the best.” She drops the cage and climbs over you getting back to kissing.

You make out with her for quite a while. She’s a hell of a kisser and a real slut. She licks your neck, teases your ears, and repeatedly gives little tugs on your chastity cage. You melt into her and don’t even notice me walk in.

“Showtime,” calls Daisy as she turns to see me. She pulls back off of you and gently lifts your shoulder to torn you to the edge of the bed. Almost instinctively you sit up so your feet land on the floor and your knees are up high due to the short bed. As I walk to you with your head at the same level as my pants’ zipper the moment becomes surreal.

“Has she been a good girl?” I ask Daisy.

“Oh yes,” she replies, “Lilly here is a real slut. I love playing with her.” Turning to you she adds, “And you know what to do now.”

With shaky hands you undo my belt, unbutton my pants, and slowly draw my zipper down. My cock flops out and you briefly pause.

“You know what to do,” blurts Daisy, “give it some kisses.” Following her direction you lean in and start by kissing the tip. I reach out to Daisy’s face and she sucks the tip of my thumb into her mouth. What a whore. I love her.

My cock increasingly stiffens from your kisses and eventually you wrap your lips around it and suck it down. Long, slow slurpy sucks follow until I push your head back. I take two steps back and out of my pants which I kick to the side.

“Get off the bed and kneel,” I say. You slink forward obediently transfixed on my firm cock glistening with your saliva. “Is this what you want?” I ask.

“Yes – yes, sir,” you reply.

“Well then enjoy your first blowjob”

That is all the encouragement you need. Easing forward you once again take my dick in your mouth and begin to suck with a fervent desire. Jack hammering all the way down just as you practiced with dildos and sucking hard as you pull back up. You feel Daisy cuddle next to you putting just a little pressure on the back of your head with one hand and once again tugging on your chastity tube with the other.

“I think she’s really enjoying herself,” says Daisy who pushes your head to one side of me so she can lean in. Her lips and tongue slide up and down one side of my shaft with you on the other. At times you pause to kiss each other. It’s wonderful and playful. I can tell you are lost with the fireworks in your head.

Eventually Daisy pulls back and tells you, “Finish your job, sweetie.” You return to mouth humping my cock and you go for the gusto, bobbing up and down and twisting to get me off. Soon I’m ready and I gently push you into position as I hold your hand on my cock and help you jack me off on your face. I cum everywhere. Mostly in your mouth but streaks of my man goo coat your face.

As soon as I’ve shot my load, Daisy shoves your head back on my dick simultaneously coaxing the last dribble of semen out of me and forcing the relatively controlled dollop of cum on your tongue to slosh through your entire mouth. The spooge coats your mouth and throat causing you to choke a little which only forces some into your nasal passages. This is the cum anointment you wanted. Dizzy from horniness and sensually overwhelmed by jizz you’re lost.

Daisy pulls you back off my cock, sucks me a couple times to clean me and holds you. Gently she begins sucking and licking the spunk from your face only to redeposit in your mouth through a volley of cum filled kisses. You slowly come back to reality as she gives you a long cum flavored kiss and once again tugs at your chastity tube. As you regain your senses she pulls back from your quivering body.

“You did a great job, Lilly. Daddy, I like playing with her. Can we keep her?”


Another super hot writing from our dear Mister S! ;)
Exclusively for all you gurls ;)
Not a classic story, it’s actually a sissy assignment for all sissies!
Enjoy your reading :)

Sissy Assignment: The Mirror

by Mr. S

An update and a warning. I’m not a writer. I write these thoughts infrequently and only when I have time away from my business. I don’t actively train sissies anymore, it takes way too much effort, even online. Now I just write the ideas that I like and Anna has graciously agreed to publish them. As far as I’m concerned she runs the best site on the internet and I’m proud to provide content. You won’t see my work anywhere else. On to the warning… This assignment seems simple and small but I assure you it is a mind breaker. After a few weeks you might find yourself compelled to curtsey in a public bathroom. Be warned. I came up with this years ago for an online sissy who wanted severe behavior modification. S(he) had to abandon it after three weeks because seeing any mirror anywhere began giving submissive impulses. Don’t try this unless you really want a severe change in your sissy attitude!

I thought I would give an assignment for all you little sissy readers out there. I know you’re looking for assignments to build your inner sissy self in the comfort of your own home. I know it’s hard to find a dominant out there and a home based task is the best alternative. Something easily done in a few minutes per day that really deepens your sissyhood and humiliation. I want you to purchase a mirror. It needs to be big; ideally floor to ceiling and about 1.5 meters wide. I’ll let you get a slightly smaller mirror if you must but go as big as you can. Bigger is better. I want you to put the mirror in a place with room to play and good lighting.

There are three rules and a few suggestions I have for using the mirror. The rules are firm but necessary. Adherence will help you on your path to being a perfect sissy.

Rule 1. The mirror will be kept spotless except for one intentional blemish. Every week when you clean it (and you will clean it weekly) you will leave a lipstick kiss print on it. Not in the middle where it could obstruct view but off to the side. Change the location weekly and ideally use a few different colors. It needs to be a bright, obvious kiss print. You may remove it should you have guests but the kiss print goes back up as soon as possible. You are not allowed to masturbate or even see porn without a kiss on your sissy mirror. Ideally you will have a cute pink cleaning rag dedicated to your sissy mirror. Cleaning is such an important sissy task, after all.

Rule 2. You will show deference and respect to the mirror. It is dominant over you and needs to be treated so. This means whenever you pass by the mirror or walk into the room it stands in you will stop, curtsey, and say out loud, “I’m a lucky sissy!” It doesn’t matter what you are wearing or doing. You may ignore rule 2 in front of guests, during emergencies, or if compliance would pose a health risk (i.e., carrying something heavy). If, however, you choose not to do your lucky sissy curtsey you may not masturbate for the rest of the day. Period. The purpose of these curtseys is to help brainwash you into subservience. (I will add that having a wayward maid perform 100 lucky sissy curtseys in front of a mirror is a great behavior modifying punishment.)

Rule 3. Every day (morning is preferable) you will stand in front of the sissy mirror for two minutes. If you are not wearing femme clothing you will be naked. No male clothing. I’d prefer a bra, panties, and heels but I’ll allow nudity. You will stand straight up with your ankles and knees together. Your arms will be straight at your sides and your hands will be straight out with your palms down as close to horizontal as you can hold them. Your head will be lowered and your eyes on the floor. No looking at the mirror. I call this sissy position. You’ll look ridiculous and submissive with your hands sticking out and head bowed. This is how I like sissies positioned in front of me. Got it? The mirror is an extension of a dominant. Now stay like that for two minutes and reflect on what the mirror knows of you. What you did in front of it last night… last week. The mirror sees you now even though you dare not look at it.

That’s it. No more than five minutes a day and an extra five once per week to clean. Not much of a commitment. It’s actually pretty easy. But it will wreck your brain. You’ll be behaving more sissy-like curtseying so often. And the thought of “I’m a lucky sissy” will get pushed in deeper into your sub-conscious. Note that you’ll have to curtsey as you approach the mirror for your morning two minutes. Rules 1, 2, and 3 are intertwined at that point to have an amplifying effect. But how are we going to get all those filthy submissive sissy thoughts running into your head while standing in your sissy position?

The area in front of your mirror is now your sissy play space. It’s where you will do all the disgusting sissy training you crave. With that big mirror you’ll be able to see all the action and replay it in your head the next day while standing in front of the mirror.

First, and most obvious is to put a suction cupped dildo on the mirror and get to sucking. You’ll see all the action and the gleam in your eyes as you practice for Mr. Right. This works so well to reinforce your position. Actually seeing yourself in action and contemplating it tomorrow. Why stop there? Get three or four suction dildos. There’s plenty of room on the big mirror. Why not simulate a big sissy blowbang and have more cock than your mouth and hands can tend to at one time? Mr. Mirror’s going to know just how eager a slut you are.

Consider your feminine movement. Dance studios have huge mirrors to let dancers see their moves. Consider learning to dance (obviously I mean stripping and twerking). Consider the most elegant way to remove your thong for a man. Bring your porn in and watch it there. Use porn as a training tool. Mimic movements and get it into your head that you need to break new ground for slut training.

One of the side effects of this mirror training you will rapidly discover is an eagerness to dress better and primp better. Seeing your every action will cause you to think about expanding your wardrobe and makeup. During your daily reflection you might have thoughts like, “I would have looked better with painted nails,” or, “Those heels could be higher,” or “I’ve always wanted fishnets.” Well good news; you can play dress up all day with your mirror. And all that curtseying might just push you into a new maid’s uniform or over the top ruffled sissy dress. Maybe you’ll really sizzle in latex or as a redhead. That mirror will push you in so many directions it really will own your mind.

You’re also going to have a shift in your choice of sex toys. Through watching and reflecting on your sissy play I’d wager the dildos will get bigger and vary in skin color. The plugs will get bigger and maybe prettier. You might find you want to get a lockable sissy collar to simulate being collared by a live dominant. You might feel a need to spank yourself until your ass is nice and crimson. Don’t shy away. Add toys and furniture to your heart’s content.

The most important piece of this training comes in should you ever meet a man. You can show him your play space and tell him he will get the same respect and devotion the mirror gets. If he’s even remotely dominant (and what guy with you wouldn’t be) he’ll love that you’ll curtsey in front of him and stand in sissy position. He’ll know you focus so hard on visual perfection you’ll really put on a show for him. And what guy wouldn’t want to hear you ask him to sit sideways to a mirror because you get turned on by the idea of tilting your head and seeing his cock in your mouth?


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