Category: Sissy Story

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?”


It’s been a while since we had our last sissy story!
There is no better timing to read a story than on a sissy weekend ;)
So tonight I got a pleasure to present an exclusive story by Sara!
What’s so special about this story is that it’s a true story!
I know that reading about Sara’s experience will inspire a lot of sissies ;)
So gurls enjoy!
Sara, thanks for the mention!

Play Day for Sara

by Sara

June 2, 2015

It doesn’t happen often, but an opportunity opened up for me recently to take a day off to get a
hotel room, get dressed, and entertain men.

So I took it.

When I discovered I would have this day to myself the previous week, I ran the following ad on

“Get ready boys – t4m super horny cd coming to town on Tuesday of next
week. I’ll be hosting at a hotel in midtown. Unlike just about every other t on
here, this isn’t a pay for play proposition (although it could be a pnp
situation). The only currency I want is hard dick.
Safe play only.
Looking to host from 10 AM to 6-7 PM. Will post more details on Monday
after I go shopping. Revealing pics to all serious inquiries.
Fill my holes and let me make you cum.
Everybody wins.”

I followed up with much the same ad with pics when I checked in. During the day, I got over 50
responses. What to do?

As you begin to respond, you soon discover that some are just chatters, and even though “all
day” sounded like forever at the beginning, time becomes a precious commodity when you are
juggling responding to the barrage of incoming e-mails, putting on the finishing touches, and
pleasing yourself with a dildo (such is the life of a sissy).

Cutting to the chase, I had enough men respond who were both desirable and serious that I could
have stayed until the weekend. Having only a day, I did as much as I could.

My first visitor of the day was a construction worker in his mid-30s. He was really nervous, just
standing there. I responded by getting on my knees, unbuckling his belt, and pulling down his
pants. I could see the bulge in his underwear. I gently nibbled his cock a couple of times, pulled
off his underwear, and deep-throated his gorgeous 7 in. rod. In no time it was as hard as steel.
He hurriedly took of all of his clothes while pushing me away. I retreated to the bed. Completely
nude he walked around to the side of the bed I was on and placed his cock inches away from my
face, and I lovingly sucked his shaft and balls. I could feel it throb from time to time, and I thought
he was going to come in my mouth when he said, “Let’s fuck”. I rolled away to make room for
him on the bed, hiked up my skirt and presented my ass. The next thing i felt was him flipping me
over on my back and pulling my hips to the edge of the bed. I put my legs up in the air, he held
my ass firmly in place, and he began fucking me hard. Then, with a strong thrust he buried his
cock in to the hilt, and let go of my ass so he could lean over a bit, and I was able to move my ass
up and down and massage his dick. I felt the tip of his cock as deep inside me as I can take a cock.
He let out a huge moan and I could feel him coming inside the condom. It was a big load.

Now, what happened next and how I reacted to it is one of the sweetest perversions of sissydom.
As soon as he came, his whole demeanor changed. He took off the condom, ran to the
bathroom to clean up, and then quickly put on his clothes to leave. His eyes darted around, he
looked down and said he had to get back to work in an emotionless voice, and he was out the
door and gone. While all this was going on, I laid back on the bed, KY Jelly oozing out of my ass,
watching this frenzy of activity.

When the door shut behind him, I felt a huge rush of excitement knowing that I was just a
discarded fuck toy. I meant no more to him than an artificial vagina. I soaked that feeling in and
loved it.

After some time, I got up, looked in the mirror, and saw I had work to do to freshen up for the
next visitor. When I checked the e-mail again, I had 7 new replies. The search was on for No. 2.

After my construction worker left, and I was preparing for my second caller, I showered and reapplied
make-up, tried a different eyeshadow, and put on another dress. Then, and only then,
did I clean out my ass, so luxuriant and, I confess, demeaning was the squishy sensation I felt
back there. With every step I took I felt the silky wetness in my ass cheeks, and I loved it.

When I got back to my e-mail in earnest, I went through the new messages. There was also a
message from earlier that morning from a 29 year old who sent a picture of his cock only. A new
message from him flashed up to say he was 10 minutes away. Of course I told him to come on.

As I waited, I primped in the mirror and played with different shades of lighting from the curtains.
I had started watching Sissy Dreams 3 and fantasizing about what would come next when I heard
a timid knock on the door. What walked in was a beautiful blond boy much younger than me. He
looked at me and I wasn’t sure if he would bolt given our age difference.

It’s good to remember at times like this that we live with our sissy-ness and feel naturalized to it
in a way that most men who walk through that door don’t. To us it is a delicious but by now
familiar perversion that is central to who we are. To most of them, they are doing something way
beyond merely meeting a woman, or even a gay man, in a hotel room. They are, as Lou Reed
once put it, taking a walk on the wild side, a really wild side.

So I tenderly told him he was beautiful, and in control. I was there for him if he wanted me. The
door was there for him if he didn’t. He let me know his decision when he pulled down his pants
and laid back on the bed.

Though it wasn’t fully erect yet, I could tell this was a bigger penis than the one I’d had earlier. I
began by kneeling between his legs and gently sucking on his balls. I looked up at him as my
tongue gradually made its way up his shaft, swirling around the head of his cock.

Whenever I have the pleasure of sucking a young man’s cock, I’m reminded of why it’s so
wonderful. With an older man, the little blue pill gives him the erection, but not really any more
sensation. You can literally wear your jaws out trying to get them off orally. On the other hand,
the younger man feels everything. You feel him feeling it in countless little body twinges,
involuntary hip undulations, and even the vibration on your tongue of semen stirring within his
shaft. You hear his moans.

I decided to go for the deep throat, but I hit an obstruction before I got the last couple of inches
in. I was at the wrong angle.

No worries. I moved around to his side and rested my head on his chest. I even brought my legs
around in the hope that he would start playing with my ass. Instead, he began sucking my cock.
Not a bad consolation prize.

After a fashion he fell back and stared at the ceiling, and I knew he wasn’t going to fuck me.
That’s ok. I don’t swallow but I love to take a good load in my mouth and I suspected this was
going to be a big one.

I decided to try to take him all the way in again from that angle, and this time it worked. He was
all the way through my mouth and down my throat, which I used to massage the head of his cock.
As I began pulling up, the first thick rope of cum flew though my mouth. I immediately quickened
the pace of my movements on his cock as my mouth filled up and then spilled over with cum. I
buried my face in his groin as I sucked out every last drop. I was thoroughly glazed from the neck
What an incredible, glorious, sensational and delicious mess. When I felt him completely relax I
laid on back on the bed, my head next to his loins, staring at the ceiling, feeling the sticky wetness
all over my face, and little streams of cum dribbling down my cheeks.

After a while he got up and went to the bathroom. He returned with a wet towel and gently
cleaned off my face and neck. Then he kissed me.

The first man made me feel like a gurl. This man made me feel, if only for a fleeting instance, like
a girl.

After a short interlude, he too got up, dressed, and took his leave. And I was again alone.

For a time I just stayed there, flat on my back, looking at the ceiling, torn between a desire for
my next dick and a desire to reflect on what had come before. I took a deep breath and
wondered… after a life of heterosexuality, how did I end up here in this obscure hotel room
inviting strange men over to ravage me? Dressed like a woman? Taking cock like a woman?
Obsessed with make-up and dresses? As turned off as ever to two gay men having sex, but unable
to quell the pit of excitement in my gut from the femininity, such as it was, I brought to these

My thoughts returned to my sticky face. Despite the best efforts of my young blond lover, I was
still glazed with cum after he left. The girl quickly changed back to a gurl. I leered over at my
computer…I was hitting my stride. I wanted my next dick.

Before I went to the shower, I checked my Inbox. A handsome black guy in his mid-30s,
professional looking, had written first thing that morning. He had meetings until 2. He had written
to say he was done. I told him I needed about an hour and asked him to pick me up some poppers
on the way over.

I took off all my clothes and stepped into the shower. I let the warm water flow down all over
what I imagined to be the feminine contours of my body. Once I was squeaky clean, I dried off
and sat in front of the mirror again for make-up. Earlier in the day, I’d gone pretty slutty. I opted
this time for something not quite so overdone….more earth tones in the eyeshadow, more
conventional red for lipstick rather than the hot pink, a bit less blush. I was very pleased with the
results, and how used I was getting to applying makeup. It was becoming second nature. The
thought made me feel like I possessed a certain femininity….not inherited from nature, but rather
earned, as if I was being rewarded for my desire to shed my masculinity by this brief incursion
into the world of girl…the hair, the makeup, the panties, the clingy bodycon dress, the hourglass
figure with the aid of a bodyshaper….as if the mother in Mother Nature was saying to me, “Yes
Sara, you may stay and play with us, like us, as one of us, for a short while.”

I was shaken out of my reverie by Derrick’s sharp knock on the door.

I let him in. Just as he appeared in his pictures, he was about 6’3”. He held me close and we
kissed. His body was hard, and I could tell before he took his shirt off that he had one of these
zero fat muscular physiques that are almost impossible to find with white men.

In no time he was on the bed naked. I remained fully clothed. We kissed for a while longer while
I fondled his rocket. It would be the biggest, and hardest cock I had all day. I gradually made my
way down to it, teasing his chest and then abdomen with my tongue. I then took my first poppers
hit of the day…a long drag I held deep in my lungs.

As I exhaled I immediately felt the poppers’ urgent command to suck. I lay my lily white blond
face on his stomach, and lost myself in the wonders of his black shaft. As I sucked, I thought about
how this really was the ultimate act of intimacy…to give a man your mouth…in such close
proximity to your sense of smell…of sound…of sight. The penis is “with you”, if you will, in a way
that is so much more intimate than when you are fucking. And don’t get me wrong, I love to be
fucked. But when you fuck, the dick is “down there”; often you are on your stomach and you
can’t even see what is happening. When you are sucking a man’s cock, it is “there”, right there,
in sight, sound, smell, and of course the tactile feel of the organ on your tongue, in your throat.

I also think for a sissy the oral experience carries a certain sweet ecstasy because it is the one
thing we can do just like a girl does it. As much as I love anal, and as grateful as I am for the
experience of anal, it is, dear sissies, an approximation of what true girls feel in intercourse. It is
nonetheless what we have, and it is beautiful.

It wasn’t long, though, before Derrick lubed up his fingers and started probing my ass, and my
immediate reaction was an intense desire to let this man’s cock take my ass however he wanted

His only words. “Baby. I think it’s time.”

He stood up and put on a condom. My bodycon dress was up around my waist. I writhed as I
looked up at him…expectantly, lustfully. He reach out for a pillow, and I first thought he was going
to place it under my ass so he could fuck me while I was on my back. Instead, he handed it to me
and said, “Here. You’re going to need to bite this from time to time….turn over.”

I did as I was told, a pillow biting slut with my ass up in the air.

Derrick put lots of lube both inside me and throughout my ass crack and around to my little clitty.
He laid on top of me and rubbed his dick in my crack. My hips thrust up to meet him. In the midst
of one of his downstrokes, his cock effortlessly slipped in my ass. He went into the hilt. It hurt. I
bit my pillow.

At that point I fell into a chasm of sorts where one loses a sense of time and memory gets blurred.
He pounded and pounded. I pressed my sphincter on his dick to get a super tight grip. Before we
had started I asked him to video me being fucked by him. Watching it later, the room was too
dark to see much of anything, but the audio it produced was one of unrestrained off the leash
passion. I was crying, I was moaning, I was begging, occasionally screaming even….I remember
thinking I couldn’t last any longer and simultaneously hoping it never ended, riding a razor sharp
wire that separated pleasure from pain.

Finally, he exited and quickly flipped me over. His condom was gone and his dick was in my face.
He was jacking that magnificent organ to climax. I obediently laid back and opened my mouth
wide. It wasn’t long before he started coming…and coming…and coming. It was on my chest, all
over my neck, in my mouth, in my eyes, in my hair. As his pace slowed, I lovingly took his dick in
my mouth and sucked out the very last drop of his cum while he writhed in pleasure. When I was
done, I looked up, and though all the cum, I smiled.

I don’t know where the words came from, and I still don’t think I fully know what they meant,
but they were out of my mouth before I knew I’d said them.

“I love you, daddy.”

After Derrick left, I realized I only had another hour or so before I had to close up shop. There
were more men than I could ever see or answer begging for a shot. I wrote five of them back and
told them the same thing…that I’d just been ridden hard and hung up wet, and I wasn’t cleaning
up for them. If they wanted to come over, I said, be prepared to find a whore that looks and
smells like a whore.

I wanted to finish the day like that. No more perfume and primping. I wanted the smell of cock
and cum all over me. I wanted the taste of cum in my mouth. I wanted that squishy just fucked
ass. And indeed, when I stood up to walk across the room, I felt fucked like I hadn’t felt all day.

I had two takers. I asked them if they wanted to do a threesome. One could be there in fifteen.
The other in a half hour. Jerry got there first. He was in town on business, he said. He leered at
me and said, ”You really are a cock-slut aren’t you?”

I replied, “If you can think of another reason why I’m in this hotel room in the shape I’m in having
just invited you and one other man to come tag team me, I’m all ears. But yes, I think you had it
right the first time.”

We left the door cracked so the other member of our party could come in and join us when he

He pushed me down on the floor against the wall and pulled out his cock. I took a long hit on the
poppers. “Suck it“, he commanded.

So there I was, dick buried in my mouth to the hilt, mascara streaming down my face, saliva
everywhere, an uncontrollable pit of excitement rising from my stomach. I know what I looked
like. It was almost as if I had an out of body experience. As I looked down from above I was the
slutty truck stop whore who had suck my cock years ago. I was the stripper I had picked up and
banged all night with two other friends back in my mid-thirties. I was every man’s whore. And
that is exactly who and what I wanted to be.

Jerry picked me up and shoved me onto the bed. He laid down beside me and I continued sucking

I hadn’t even heard Sam come in (heck – I’d even forgotten all about him), and I jumped a bit
when I felt an unexpected second pair of hands fondling my little bubble ass. I could tell Jerry was
close to coming. I pulled up, rolled over, and looked at them both with eyes that tried to tell them
they could do anything they wanted to do.

They must have gotten the message. Sam laid on the edge of the bed, his feet over the side, and
said, “Ride me.” Because I really am a cock slut I knew exactly what that meant.
Reverse cowgirl.

I bounced up and down on his dick, while Jerry came around and stuck is dick in my face. So I
could suck Jerry, I quit bouncing and started a slow circular undulating grind on Sam while I
hungrily swallowed Jerry. My pussy was gushing wet. Suddenly, Sam grabbed my hips and
directed them front and back across his groin. That made his dick tease the back end of my
rectum in the most pleasant way, and I aided his movements. I heard him groan, and I felt a
gusher inside me. After he finished, he tossed me off and I laid there on my stomach. Jerry then
hopped on and proceeded to mechanically fuck me. I didn’t care. I was exhausted. I was spent.
There was no more physical pleasure to be derived, just the emotional pleasure of knowing my
sloppy wet boi pussy was being used by another man to come to climax. I was a human fleshlight.

When it was time, he shot his come on my back. I didn’t move.

As Jerry and Sam hurriedly got their clothes back on, Sam said to Jerry, “I can’t believe we just
did that”.

“Yeah.” Jerry replied, “God, look at her.”

I smiled inside….because he’d said “her”. I never even turned over to say goodbye. They never
said goodbye to me. Instead, Sam said to Jerry, “Let’s get the hell out of here.”
And then they were gone.

Cum was dripping out my ass. Cum was dripping off the side of my back. My face was sticky with
drying saliva and pre-cum. My breath smelled like dick. I know my ass smelled that way as well.
My underwear was all torn to shreds. My leopard print bodycon dress was covered in cum stains.
My pussy was sore…comfortably sore…..achingly sore….lustfully sore….I couldn’t decide. I just
know that I loved it.

The light of the day was starting to dim outside. Soon, I’d have to shower and pack and go back
to my other life. Before I did, I tried to make some sense of what it all meant. I recalled at the
beginning of the day, when I first looked in the mirror…how fresh and feminine I felt. I remember
thinking that I wished my dick would just fall off for good, right then and there. I felt a lump of
excitement, quite muted but still there, thinking about the next time. Kind of like the conclusion
of Sissymaker II, when the organ gradually comes back with a muted pulsation while a sissy rides
a dick.

I thought how this had all started in 2004, when on a lark I decided to go to an adult theater to
suck a dick instead of a strip joint ….how it then took me a couple of years to figure out that I was
a bottom….how I used to spend so much time on Ass4All watching Heather Brooke and Amber
Michaels suck and do anal, trying to put myself in their bodies….but still thinking of myself as a
man being fucked by a man.

Of course, like so many, the great transformation came when I discovered Annamalice. A year
into Annamalice, crossdressing was just a fantasy….but then it wasn’t. Meeting men in hotel
rooms dressed up like a woman was a fantasy, but then it wasn’t. Going out dressed like a woman
on out of town trips dressed up like a woman was a fantasy…but then it wasn’t. Having the
courage to present myself with wig and wardrobe at a MAC store for a total makeover, from
which I then proudly walked out to my car and drove to the nearest porno theater and took over
the joint as the reigning theater slut….it was all a fantasy, and then it wasn’t.

The one thing I knew for certain is that I would always be back. Once you’ve done this, it has its
hooks in you… just like it says on Sissymaker, there really is no turning back…it’s just a matter of
where and when you have the chance to indulge your sweet tender precious sissy perversion,
knowing how richer your life is because you’ve lived this, and secure in the knowledge that you
will live it again.


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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