Category: Sissy Story


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?

2702

It’s been months since the last story I posted…
So I got a new one for you gurls ;)
And it’s a new story by Mr. S!
And you know that you can always expect great and original stories from Mister’s point of view when he’s writing them ;)
I like how he speaks directly to you… to a sissy! ;)
Enjoy!

Helping A Friend

by Mr. S

My longtime friend Steve has been on a string of bad luck. He’s nothing but a drone at work and to cap things off his girlfriend just left him. Best thing possible, I thought. The bitch never took care of his needs and he just lost the confidence to demand any sex. Worse, she refused to give him head. I don’t know how a man could live like that. When I met him for lunch he seemed slumped and weak, hardly filling his suit and almost smaller in the shoulders. We’ve known each other since college and it pained me to see him like that. I suggested a vacation but although he has plenty of money he just can’t get away from work. I suggested we go out for drinks and maybe a little flirting with girls. He told me he just wanted to be alone. Knowing I was running out of ideas and fearing his depression, I pulled my final card. “How about you swing by my place on the way home tonight and let my sissy give you the blowjob of your life?” He knows our arrangement but still hardly reacted to the offer. Still he hadn’t said no. Not giving him the chance, I finalized it. “Done. We’ll expect you around six.” Steve stammered a bit but reluctantly agreed.

“Now don’t forget, sissy. He’s distraught and a little lost. I want you to do everything in your power to wake up the man in him. Encourage his dominance.”

“Yes, sir. I’ll put all my talents to work,” comes your quick reply.

Shortly after six Steve arrives and I greet him at the door with a tumbler of Scotch. We chat and I invite him into the sunroom. He practically falls onto the sofa with his eyes closed and I decide to let my girl do the work. I zip back to the kitchen and send you in. As he opens his eyes he sees you wearing a blaze red bikini with matching heels and lips. Perfect to wake up his inner desires. He adjusts a little but you’re on him quickly, kneeling on the sofa over him. You gently tug on his shirt collar while grinding your hips and whisper, “Like what you see, baby?” He slowly nods a little and you deftly spin around and rub your ass into his chest. “How about now, any complaints?” Steve meekly looks down at your beautiful red bottom with its ruched back rubbing on him and murmurs under his breath. You pick up on it immediately and look over your shoulder at him. “What could I do better for you, sweetie?”

“Oh, it’s nothing. I just would’ve preferred a thong on you. No big deal.”

“Well,” comes your reply, “Why don’t you just give me a little wedgie?”

Steve is dumfounded but slowly lifts his hands to your bikini and gently pinches the fabric. Exhaling nervously he gives them a little tug and pulls them right up your ass crack. “Oooh!” you squeal, “That felt great. Is that better for you?”

“Yeah, that was fun,” he replies.

Swiftly you kick your legs to one side of him and lay across his lap. “It’s been my experience that thong guys also like to spank. Why else have my butt exposed? Wanna give me a spanking for being a naughty sissy slut?”

“Umm… OK.” Steve hadn’t anticipated this and gingerly slaps your but cheek with no force at all.

“You should spank me harder than that,” you reply as you wiggle. “I want my butt red and burning while your cock’s in my mouth.”

The next series of spanks comes harder and harder as Steve gets comfortable with the fact that you can take a good spanking. As the smacks rain down on your unprotected ass you whimper and squirm adding to the ambiance. Eventually the spanking stops and Steve rubs your bright red ass.

“Does my butt match my outfit?” you giggle as you sit back up kneeling over Steve, facing him. He keeps his hands on your ass still rubbing and tracing your bikini down your ass crack. “It feels so good to feel your wedgie and spanking. Pleasing you makes me so happy.” He keeps rubbing and slowly gets near your asspussy. Quickly you grab his hand and bring it up stuffing his index finger into your mouth and suck it a few times. As you pull it out you tell him, “Go ahead, put it in,” with a wink. He slowly works his finger in and you ride him, bouncing on his finger for a few minutes. You moan and purr and tell him how he hits that “sissy spot” perfectly. You pull your top aside revealing your small hormone tits and pinch and squeeze your nipples right in his face.

After a few minutes of riding and grinding, Steve seems to loose intensity and you pull his finger out and shove it right back into your mouth to clean it. “My ass tastes great on your finger. I think you have a little bit of an ass fetish, honey.”

“I suppose I do…” trails Steve as you get up and go to the endtable and return with a butt plug with a remote. As you lick the plug to lube it you tell Steve, “You hold the remote and turn up the vibration when I’m being a good girl. Try it.” You hand him the plug to test, turn around, get on all fours, and one by one kick your knees up on the sofa straddling Steve. “Go ahead and put it in, sweetie.” He pulls your bikini aside and slowly works the plug into you. Without being prompted he tests it, going from low to high a few times and each time you purr and moan. When he’s satisfied that it works you nimbly stand up but before turning ask him, “Could you make sure my wedgie is tight again? I want to be perfect for you.” This time he firmly grabs your bikini and yanks it up with some force. You jump a little, yelp in surprise, and smile because you have brought back his dominant side. Time to start the real show.

You spin and drop to your knees and bury your face in Steve’s lap. Through his trousers you kiss, lick, and rub your face over his stirring cock. You unbuckle his belt slowly and unbutton his trousers. As you slowly pull down the zipper with your teeth the vibrator rumbles to life in your ass and you moan much to Steve’s pleasure. His cock flops out and you begin to tease it slowly. Light kisses on the tip and delicate licks down the shaft just to rev him up. Eventually you take him into your mouth with one long powerful suck. Steve groans and as you pop off the tip you look up to him and demurely say, “Your cock tastes delicious.” Steve smiles as you plunge back down on his cock and you are giddy knowing no woman has ever told him that before.

After a few more minutes of bobbing, Steve says, “Why don’t you take my trousers all the way off?” He shimmies out of the seat of them and you pull them all the way off and drop them on the floor. The vibrator stops. “Fold them nicely, please,” Steve scolds. You turn, both to fold the trousers and to hide your trampy smile. He’s figured out the reward system. Once folded, you return to sucking. You go through several patterns but Steve must like your corkscrew motion the best because as soon as you do it the vibrator starts buzzing again. The feedback is great. You pause momentarily to tell him, “I love that you control my ass,” and go right back to corkscrews.

After a while the vibrator once again goes silent and you pull back, jerking Steve’s cock with one hand while looking up into his eyes. “What can I do for you now?” you ask.

“Why don’t you lick my balls for a while?” he responds.

“I love licking balls. They hold my prize,” you tell him as you dart under his cock and start lapping at his nuts.

“Is there anything you don’t like doing?” Steve asks, half joking.

“Displeasing you,” comes the quick answer between laps. The vibrator buzzes on.

This continues for a while with various methods of sucking, licking, and teasing. Eventually Steve stops the vibrator and looks down at you saying, “You know, I’ve never been deep throated before.” Before he can finish the sentence your nose is bumping his stomach and you’re straining to tongue his balls. Up and down a few times.

“You could hold my head down if you like… Some guys enjoy that.” Steve does and eventually he develops the confidence to hold you down until you gag and choke. As you sputter and drool on his cock you once again feel the vibrator hum telling you what a good girl you are. This is the heavy work that causes the slobbering and tears that really cement sissy cock submission. Your very breath is controlled by cock and you love it. Best of all Steve is really asserting himself, not caring how hard he is on you.

Eventually he pulls you back and stops. “I’m getting close to cumming.”

“Where would you like to cum? Down my throat? In my hair? On my face? On my tits?”

“I’d really like to cum all over your face.”

“Can I swallow it all afterward or would you like me to let it dry on my face so I smell you the rest of the day?”

“I… figured you would just towel it off…”

“I would never waste a drop of your precious jizz, sir.”

Steve seems taken aback by this response but gets out, “Well then you can swallow it if you like.”

With that you hammer right back down deepthroating. Steve must have liked the options as the vibrator maxes out. Soon you feel his balls tighten and he announces his need to spooge. You pull your mouth back, position your face directly in front of his cock and jerk him with one hand while caressing his balls with the other. You encourage him saying, “Oh yeah, baby. Gimme that spunk facial I want. He erupts creamy globs of cum and you swing his cock around painting your entire face. As soon as he stops cumming you clamp your mouth on his cock sucking the last drops out and extending his climax. He falls back into the sofa exhausted.

“Good job, baby,” you encourage. You sit back. “Take a minute to admire your work?” Steve looks at your well coated face and smiles. You pause briefly, smiling before you begin pushing all his cum into your mouth using just one finger. Slowly you work it all in and lean in just a little to show off how much is there. To Steve’s amazement you flick your tongue around and gargle his jizz before shutting your mouth, swallowing in one gulp, and opening to prove it to him. Once done, you eagerly tell him, “Your jizz is delicious. That was wonderful.”

“I’ve never had a blowjob that good or intense,” Steve lazily admits. “I wish that all girls were that dedicated.

“The fact that all girls aren’t that dedicated is the reason sissies exist. Could you do me a favor and turn off my butt buzzer?”

“Oh! I forgot it was still on.” The vibe shuts off.

You reach back, pull the plug out, and begin to lick it clean. Steve is noticeably turned on.

“Maybe I need a sissy,” he muses as you lick and giggle. You’ve done your job well and look forward to a reward from me. He’s happy, eager, and horny even though he just had the best orgasm of his life. Thanks to your good work Steve looks like a new man.

2690

Hey gurls, for today I want to publish a nice illustrated true story by Slutty Chrissy…
For all the sissies who loves gloryhole stories ;)
Chrissy also produced one of the videos posted a long time ago: #501 – Sissy trainer by Slutty Chrissy
Enjoy your read and also visit Chrissy’s blog: http://sissychrissytgcaptions.blogspot.com

Gloryhole first timer

by Slutty Chrissy

This is a true story of an experience I had last week. I hope you enjoy!

It all started this past Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store.

I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel of all the different fabrics and the unique, incredibly sexy smell that is a combination of stripper perfume and sex toys, with just a hint of dirty old man thrown in. There is nothing hotter than that smell. Well, almost nothing – but let’s not get ahead of ourselves. I picked out a cute little black dress, a pair of matching velvet and lace panties and a black teddy with a skull print all over it.

I went back to work, and snuck into the bathroom to try on my new teddy. I spent the rest of my day wearing a teddy and thigh high stockings.

I felt so sexy, I just wasn’t ready to go home when I got off work. I headed to a local strip club – I figured maybe a lap dance could be fun – some hot stripper noticing that I was wearing lingerie under my clothes should be sufficiently humiliating for a sissy like me.

I wandered around the strip club’s adult boutique for a while – looking at their lingerie and sex toys. I was getting ready to head to the main club when I realized they had a “movie theatre.”

I had been to this club before they remodeled and they had a bunch of booths and a small theatre with 2 TVs and some couches and since I hadn’t checked out their new theatre I thought “Why not?” I was expecting a small room with a couple of couches and a TV or two, but what I found was a row of booths.

I took my time strolling down the hallway, noticing the tell tale stains on the floor of each booth – some dried, some fresh – and noticed the hard plastic chairs hastily shoved into each booth. When I reached the end of the hall I noticed that the chair in the last booth was plush and inviting. Since none of the booths were in use I grabbed the comfy chair. I quickly stripped off my boy clothes and threw some money in the video machine.

I scrolled through the videos until I found one of this hot brunette bimbo with huge tits, servicing three cocks at once. I was so jealous of her – not jealous of the men getting their knobs polished, but jealous of this bimbo who had 3 cocks all to herself, and I had none. I turned a little in my chair to get more comfortable… and that’s when I saw it. What I had wanted to find for so long – a gloryhole!

Before this club had been renovated there were no gloryholes and they strongly discouraged “cruising.” I never expected to find one now. I stared in stunned silence. Holy crap! A gloryhole! And then the cruel twist of fate dawned on me – the theatre was empty. There I was all dressed up, horny as hell and ready to suck only inches away from that magic portal that would deliver cum-filled cocks. But there were none to deliver. I resigned myself to my circumstances, pausing for a moment to wipe my finger in a fresh cumstain on the floor, tasting the bitter salty sweetness of some stranger’s seed. I found a full condom on the floor too and dumped its contents on my chin, loving the feel of it sliding down my neck and pooling on the fabric of my new teddy.

But then I heard the theatre door open. I kneeled down on the floor (putting my stockings into another puddle of jizz!) and put my eye up against the gloryhole. Someone entered the booth next to mine. I was so excited I didn’t know what to do. I had never done this before! I sat back in the chair and waited – paralyzed in excitement and fear. I saw an eye peering through the hole and decided to give him a show. I did the sexiest little dance I could muster, then bent over and wagged my tight ass at him. When I looked back the eye was gone, but I hadn’t heard him leave, so I stuck a finger through the opening and gave him that “come here” motion. As soon as I pulled my finger back there it was. A cock. Some anonymous stranger’s cock. I did what any good sissy would do and wrapped my lips around it.

He was a little soft at first, but I quickly felt him harden in my mouth. I bobbed up and down on his cock, licking his shaft, slobbering all over him. I took him all the way in my mouth until my face was pressed against the hard plastic wall of that booth. He began to pump in and out of my mouth, face fucking me like the dirty little whore I am.

Before I knew it I was alternating between swallowing his cock and begging him for his cum. LOUDLY begging. Like some desperate gutter slut who had to have it to survive. Like a junky needing a fix. I felt him jerk in my mouth and then the first spurt of his hot sticky load showered down the back of my throat. Wave after wave filled my mouth, until I couldn’t keep up and I began drooling cum down my chin.

When he had finished depositing his cum in me, he pulled his cock back through the hole and left the theatre. I slumped on the floor, spent from my first gloryhole blowjob. I sat there, with yet another load of cum on the floor soaking into my panties, my random stranger’s cum beginning to dry on my chin, neck and chest. It was a glorious feeling and I took in my surroundings. On the screen some random pornstar was blowing bubbles with the cum that had just been deposited in HER mouth.

Only this time I wasn’t jealous. I had my own cumload to play with. So I joined her.
I then got dressed and headed out, cum still glistening on my chin and neck, the acrid salty taste fresh in my mouth.

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