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transformation of evelyn
I moved forward in the line, clutching my package of panties, brassiere and camisole rolled into a tight bundle so no one could see.

Perspiration was running down my back, over my freshly shaven chest and down my thighs – causing a sloppy slipping between my legs as I shifted from side to side. Finally! I make it to the register. I place the items on the counter along with a sealed envelope. A note, specifically decreed from the House of Sissify given to me just for this shopping assignment. My mind fills with doubt – but thinking of all my long held desires, I pull up a little assurance and move forward.

The checkout lady is in her mid-forties who’s name tag reveals Jill – a bit taller than most with a deep and lilting voice. She is dressed impeccably, as one would only see working at such a fine ladies store. She unrolls the bundle. She takes her time opening each item fully on the table, attempting to remove any wrinkles from the fine lingerie created by my abusive grasp. Carefully looking at each of the labels, she then looks into my face and says;

“Honey – you didn’t even try these on. There is no way these pieces of lingerie will fit you. With three different sizes here – I don’t think they will fit any one person at all.”

Immediately she gets on her intercom and calls out:

“Assistance needed at counter 6, assistance for counter 6”.

Baffled, and embarrassed – the sweat still running down my shaven legs – I squeak out a small,

“Uh.. what’s wrong?”

I thrust the special sealed note to the checkout lady who picks it up with her finely manicured fingers, and neatly places it into her pocket without even looking at it.

“Can’t I just pay for my things and leave?”  My voice is trembling

”Your things!?”, Jill retorts with a gruff laugh “These fineries will in no way fit you – so I am calling for someone to take over my register here so we can fix this pathetic attempt at sizing and get you back to the dressing room and get you properly fitted and prepared.”

I’m, blushing and nearly hyperventilating uncontrollably – yet I feebly utter:

“But, I, I, i….. “

“Nonsense!” says Jill, “You’re not the only sissy who has been sent here – we have a special room set aside just for you girls. A room where we can give special attention from our dressers and team – we’ll have you properly dressed both inside and out in no time at all. Now, come along!”

Jill grabs me by the elbow, and escorts me down the hall. Her heels click on the hard marble floor with each step.

“What’s the name honey?” Jill askes her voice husky and warm.

Muttering so no one could hear, “Drew?”

Jill giggles

“I’ve never cared for that name”, Jill laughs, “But, it doesn’t matter anyway – your new name has already been chosen and after we’re completed here, no one will think of you as a man, nor care to remember you were ever other than you will be after today!”

What did she say? Did she just tell me nobody will think of me as a man?

Twirling, she leads drew toward the back of the department store, she bursts forth with another peel of laughter.

As I walk a few steps behind her now, I notice how safe and secure I feel. It’s kinda like being taken to the nurse’s room in school to get out of class, or… like Mom was going to take care of me. I think it’s going to be ok after all.

Suddenly Jill spins around, and exclaims:

“So, sissy, here we are! The start of the rest of your life!”

What? My breath escapes my lungs, as that warm and fuzzy feeling of security vanishes. I’m sweating again, my hands tremble, my knees feel weak. I find myself gasping for breath as these fleeting feelings of security give way to overwhelming fear!

What is going on? My mind races. Did that note do this? She didn’t even open it! Is she part of the House of Sissify? OMG, I am going to get caught and I’m gonna lose it all. Yep. Everything. My wife. My job. My life. Oh fuck. Why do I let my fantasies overtake me?! What the hell did that note say?

“I am not doing this….” I begin to stammer

“What will my wife think? Where is Joyce?” I look around quickly for her. For anything that can save me.

I realize instinctually, I was calling for her like my mom to fix this situation that I had lost control over.

“Joyce?”, says Jill, “You mean your Superior.“

“Um…My wife”

“Ha!”  Laughs Jill, “Poor thing, I guess you would still think that…”

“How do you… how do you know about Joyce?”  my voice is weak and trembling.

“Obviously, your Superior is involved in your Training! It’s Joyce who sent you here in the first place.”

“Now you don’t really think this cute idea of wearing panties was your very own do you? Like you just happened to find the House of Sissify while surfing for porn?”

“Oh… fuck…” I stammer, my passion colliding with my trepidation, the fantasy running straight into my fears.

“She contracted with the House of Sissify to take over your internet, and feed you subliminal hypnotic feminization keys until you joined the House and told them all your fantasies. Every sordid one of them. We have them all.”

“As for all this Wife/partner/ possessive, patriarchal misogynist nonsense, do be certain that from now on She is your Superior!”

I was scared. It was starting to really sink in.

“That look on your face tells Me you finally realize the predicament you are in. You’re being humiliated & transformed to teach you a damned good lesson and to eventually become a well-trained sissy designed for Her personal amusement.”

I couldn’t believe what I was hearing!

“But first we need you to get cleaned up and get that boy off of you! So come on in to our first phase, come on.. come on.. “

Jill grabs drew by the hand and walks him sheepishly behind the first door.

My mind is racing! I’m excited, scared, massively turned on. Massively… Ashamed. Ashamed?  Is Joyce really here too? How could this be? It must be, because I joined the House of Sissify!

Will I be transformed without responsibility? Will I be feminized, even against my will?

drew begins to hyperventilate, his heart is pounding in his chest, his tucked bits pushing uncomfortably into his gaffed and pantied bottom.

Drew follows Jill into a small dressing room with a hot pink velvet chaise lounge atop a white furry carpet.  Drew begins to tremble.

“I..   I,” he stammers  “I was just looking for some girly things,  I like the way they feel on my skin, I mean  I’m not really looking to be a girl.. I mean..”

“A Girl!?” Jill quakes.

“You think we are turning you into a girl?!!”

“Ha ha.. honey, no no, no, you are not a girl, you will not be a girl, you will never be a girl, you are in fact a sissy!”

Jill’s, force is amazing, drew muses on how much he loves it when she is so forceful, how like Joyce she is, and how, indeed it was Joyce’s idea that he come to this new store to get some frilly things so he would stop stealing hers.

“A sissy? What kind of a sissy?  I mean other than a taunt for an effeminate guy, what does that really mean?”

“Well, honey, you are a sissy, not really a man at all, and certainly not a real woman. A sissy is a play thing, a delight when well trained and behaved, a joy to its Mistress, and an object of derision when it is uncontrolled.. by the way, how do you like being referred to as it?”

“I don’t really like it”

“Don’t forget – it’s always Mam to you honey. We can’t start referring to you as she yet now can we? Soon enough, but not yet, what with hairy legs and silly man bits flailing about… “

“I am already shaven and tucked Mam”

“You are?!” Jill lifts her eyes with excitement.

“Well then, we can just skip this first section of clean up if you have really learned to do a proper job. Take off your clothes. Let’s see how you have done…”

Drew stands there, embarrassed, flummoxed, frightened.

Have I really just revealed my secret to this Woman I just met?

As his dreams, hopes, fears and memories are flooding his mind and his heart thumps in his smooth chest he begins to reassure himself

I know she’s a Mistress, she is a Madame, its going to be alright. She must have my real interest at heart, and besides, the House did suggest they would have ways to get into my mind and I did give her the note, though she didn’t even seem to read it….

“DO IT!” Jill demands.

drew’s hands are shaking as he starts to unbutton his shirt revealing his chest shaven and his nipples hard as stones.

He drops his shirt and his pants, he is standing there, entire body free of hair, tightly tucked and pantied, excited, embarrassed and oddly liberated.  He giggles.

“Very nice. Very nice.” Jill replies, “Clean, well done, nicely pantied! Who taught you to do this?”

“Ah..” drew utters. “it was all in the shaving assignment,  at the House, I joined…  my Superior doesn’t yet know”

“Ha Ha!” jill laughs, “She knows, do be sure. You have been taking your lessons at the House of Sissify seriously I see, and your honesty speaks well of your progressive sissification.  We had reviewed your participation, but you had not sent in any photo’s – so, now we are here to see for ourselves aren’t we.”

“Yes Mam”

“Very good. You are properly shaved, tucked and pantied so we can move on to your deplorable lingerie choices, but first!”

“You really do know of my participation at the House?”

“That is what the House is for sissy. It’s a placement service after all.”

Jill continues to enjoy herself as she admonishes his feeble understanding of what he got himself into.

“For all of your wanking and chatting it is obvious you did not read the Shopping Assignment? How could you have purchased these items not even aware of your size?”

Jill sighs.

“At least you brought your note to ask for help. While you may have worked out how to shave and tuck your pathetic appendage, your ability to be a sissy to be proud of is far from complete.”

Drew, utters a sigh of relief, She is accepting him, as he is, she knows, Joyce knows? How could all of this have transpired from simply joining a web site?

“What will happen next Mam?” He feels any last vestiges of masculinity draining from him like his libido after release.

“We get your fitted, outfitted and presented of course. Training Training Training! Let’s see… from your profile…let me bring it up right here” Jill picks up her phone and opens up drews House profile and quickly checks his princess points and activity log.

“Hmm, not really much work here.. wanking stuff mostly”.

Jill adeptly flips through a few screens with her beautiful fingers – quickly swiping her smart phone.

“Honey – I’m getting the impression you think this is all about you and your desires. It is not!”

“No mam” mumbles drew with his head bowed.

“Sit up dear!  A sissy needs to be able to sit up straight less it looks like her breasts are weighing her down!”

Breasts? Drew perks up.

Jill is still flipping through statistics – scanning drew’s logs.

“Oh My Goddess. Have you not even tried to look at how to perform proper cunnilingus for your Superior? You should be ashamed”

“Do you not even care?” chortles Jill.

“Of course I do… I mean.. yes Mam, I do.  It was just.. I was just chatting and thought I would like to start with shaving.  I..I haven’t been there for long, you can look, really I was…. “

“I know how long you have been there.” Jill cracks with an authority that seems so very matter of fact.

“We know what you have been doing with your time. How much time you’ve spent being helpful and being your natural subservient self and how much time you spent looking at the real men images on the site… even reading through some of the cock sucking assignments, and, oh look at this!”

Such a long pause. It seemed too long!

“Hmm. Yes drew; by watching your surfing habits, We have created a very complete profile of your desires and talents – as well as your weaknesses. It appears you are more interested in sucking cock, than pleasing your Mistress! Not a surprise to Her of course.”

“No Mam… uh..”

“Stop speaking when you are being spoken to!” demands Jill

“Be quiet, your voice is starting to irritate me.”

“It is in part the reality of your love for cock that your kind Superior has been working with Us to further your training in a way that will please you both.”

My mouth begins to salivate. Why does the idea of being a pleasure to my Wife and cause me to react in this way? Why do I like it so?

“The House of Sissify has been around for nearly as long as you have been alive – and it has certainly been influencing you since you and your Mistress got together. Joyce has relayed the story of how you tried on her dress prior to your bonding ceremony and how much you liked it. She knew then as did your best man – In fact most everyone seems to have known but you! It was shortly after you marriage and Joyce got control of your finances that she contacted the House. Several months in fact before you ‘discovered’ the House  “on your own.”

“In fact, it’s due to the House that we have this small transformation studio here. Lucky you!”

“While your name is certainly androgynous enough, for Our purposes you need a new name. It’s simple really – along with a new name, your old self that identified as something of worth without effort can be dissolved – and a new you can be artfully crafted. A you who earns self respect and the glance of a Superior through service and actions worthy and appropriate or her true purpose in life. It is this new name, this new you that from this time on we will all know.”

Did she just refer to me as “her”?

Drew struggles to stay standing, naked and shaven – being examined like a science project before this strong Mistress.

“So from now on you shall be only known as evelyn. sissy evelyn..”

“Sissy evelyn? How can that be? What will I do for work? Mam.”

While ‘drew’ had worked for several years in a law firm as an associate, he had always envied the women who worked there dressed in their stockings and pencil tight skirts. How, the principals each had their own secretaries who were at their beck and call and seemed ready to serve in ways that drew could only dream. So often he watched these girls smile and walk into their bosses rooms, only to come out giggling running their fingers through their hair. How he envied the ease and dynamic they expressed! But lately his boss, Jayden, has been keeping him out of the office, with paid trips with Joyce for get away weekends – turning into weeks, now up to a month that he has been paid to stay away. Drew thought it was due to his great work on that big case at first – but this was getting to be quite a vacation. It was during this time he encountered the House of Sissify. In fact, his desires to be feminized had increased even to the point where he has come to suspect some new chemistry has been happening due to his thoughts and focus. He really has been looking and feeling more of a sissy with each passing day.

“Yes, work. We do have a surprise for you there, let’s just say that your boss already knows. In fact, he has known since you started with him, and it was through his encouragement that you have been spending so much time away as you have been transforming.  When all is complete – no one at your office will even remember drew ever worked there, and now, you, evelyn, will be working directly for him.

“But! I have my own office”, says drew.

“No.  Had”, replies Jill, “Drew had an office, he’s no longer working at the firm. Evelyn will be Jayden’s secretary. And you know where she presides. From here on out, you are Evelyn.”

drew/ evelyn, is breathless with a mix of hope, desire and fear.

“How, what has been happening to me? You mean my desires and smoother skin is not just from chance?”

“Ha ha!” Jill laughs. “Chance? From you doing nothing? No, honey, your chemistry has been being worked on since you started there, it is only since your appearance was starting to change that its completion has needed to occur outside of the oversight of others in your firm.”

“So, evelyn, shall we begin?”

Poor ‘evelyn’  can’t believe what is happening, it is so fast, it is so tantalizing  s/he speaks up:

“Is it his or her for me Mam” s/he asks.

“her of course honey, you never were much of man to begin with and from here on you will never have to bother pretending again.”

“Thank you Mam… I think?”

“You think?”

Jill turns with a fierceness in her voice?

“You THINK? No, honey you don’t think, while We may use her and she as a diminutive reference to break down your silly egoic sense of pride, never presume you think. We Will think and let you know what you are to do. Got it?”

“Ahh yes Mam”, demur’s evelyn.

“A sissy is as a sissy does, and she is never more perfect than when she is in her proper place of service”, states Jill. “Now come… let’s get started.”

Evelyn is led into a room down a narrow pink hall. She is amazed that in her own mind she has begun to refer to herself as she.

The hall is the same color pink as the House of Sissify! It must be for real? Evelyn muses, feeling lighter and freer as she follows Jill past various closed doors, occasionally hearing others behind those doors, some sound like they are working with others, some sound as though lost in a dream speaking to themselves. Out of one comes two people dressed in surgical gowns, a smell of sterility wafts from the quickly closing door. Evelyn begins to dream of the potential.

When Evelyn first came the House of Sissify she had read how the House would get into her mind and life in ways she couldn’t at the time even conceive. When she first read about how the House would work to take the responsibility of her transition into its own hands she thought, how in the world could that be? But as time has progressed, and now encountering Jill and to find out that Joyce and even Jayden is in on this too?

And now she finds herself here with a Mistress who seems to know her far too much to be coincidence. she is pantied and shaven, is answering to a new name and even in her own mind has begun to refer to her herself as she. Wow!

Evelyn begins to feel weak again. Is it the hormones they have apparently been feeding her? Or just nerves she muses? Feeling like a fly in a spider web, tantalized by the potential of drew’s end and evelyn’s emergence, she finds the possibility irresistible as she walks behind Jill and into the next room.

“Now, we have been noticing evelyn, that you walk like a crab. Your big swaying steps can only mean one thing.”

“What is that?” evelyn asks shyly.

“You of course are not plugged!” replies Jill.

“A properly sized anal plug serves several purposes. Of course, it keeps your sissy pussy relaxed and ready for when it’s purpose is needed. With each step it also keeps your prostate stimulated so your libido remains strong, causing you to hunger for release – which now is of course, under our control. This will serve to control your wandering thoughts so they can be channeled properly into your complete transformation.

But thirdly is causes you to step daintily, and that is the reason today you will be fitted here by our man Pico.”

“Pico is the man on our team who helps us in this regard and since it is your first plug we thought is be best if you get used to having a real man around while sizing.”

“But  but..” evelyn stammers.. “But I like women. I am married.  I .. “

“It is not ‘I’!”, Jill reprimands. “Be humble when you refer to yourself. ‘This sissy’ is far more appropriate.”

Jill continues, “Now, I will overlook this one transgression – but given We literally have your ‘’balls’, your credit cards, your identity and  Mistress has all of your bank accounts and Your boss has already been informed – I suggest you get your pretty little head around this and submit like a good sissy”

Jill leaves the room, leaving evelyn alone with Pico.

Pico is about 6’4” a beautiful light brown color tan to his skin, dark hair, brown eyes.  Why am I looking at him like I want to be fucked evelyn thinks. What is happening.. am i really starting to change already?

“Here, have a drink” Pico, smiles as he offers evelyn a small cup. She drinks it down and notices an odd cherry taste to it.

“What was that” she asks?

“Oh, just something to get you started honey.”

Evelyn falls off into a strange state of being half awake yet half asleep.

“Now, you little sissy”, Picko says in his deep rumbly voice. “We will get you set up. This is going to be fun.”

Evelyn drifts off, as she awakes again into the half asleep state she feels a pleasant sensation in your anus, a fullness, her mind immediately goes to Pico.

She comes to notice she has a headset on, a sort of virtual reality set, oh, and it includes some thin gloves, and an anal plug and it even feels like she is in a new set of special panties. She is lying down on the lounge looking at an image of herself as a feminized sissy, clothed, smooth, pretty. She sees Pico come up to the image of herself and he strokes her arm. She feels it on her own arm. He runs his finger through the hair of her avatar and she feels a pleasant tingling sensation over her own head. He runs his hand over the avatars anus and she feels the sensation deep inside her. She loses her awareness of her body itself, for now she is her avatar.

She lies there as though her avatar is reviewing her memories. Images and memories are rising and falling away from her view. They are coupled with directly experienced feelings. She can no longer tell she is other than what she is seeing and feeling. There is her Mother and her Father, or drew’s mother and father… but they are playing with a small young Evelyn. Her father smiling sweetly at his little girl. Evelyn’s Mom primps her dress to keep her clean and standing up straight. They are talking to her. To Evelyn, they’re daughter. The scene moves, she is playing with her childhood dog, but again she is Evelyn. Now it is Easter, she is herself dressed in a plain white dress, she is giggling with the other girls, now she is dancing as a young Evelyn at her prom, her boyfriend a geeky but handsome boy looking hungrily at her, as she stands demurely wanting to be seen.

She begins to feel the plug in her anus swell, she is aware of Pico inside of her, her avatar, or is it herself, she can no longer tell the difference, he is a pleasure and he is pleasing himself.

She begins to come back aware more and more, she is still on the lounge, she realizes she has orgasmed a more fulfilling release than she has ever known and it is all on the inside. She opens her eyes Pico pulls off her head set and gloves and kisses her on her forehead.

“Not so bad was it?” he asks, his head still slightly wet with his own perspiration.  evelyn smells his funk and feels her plug again. She squeezes it with love.

How long has she been here? She looks into his eyes, he smiles, she gleams back, whatever has happened is lasting, she no longer desires to be drew, she is evelyn, and loved, just as her daddy told her she was.


Jill re-enters the room, it seems like a lifetime has past, it takes a while for evelyn to recognize and recall what is happening. She looks imploringly to Pico, his toothy smile is wide.

“See you again honey”, he says with a wink as Jill comes over to evelyn’s side.

“Your identification has already been changed just as your memories and desires were being rewritten. I suggest you get any remaining silly ideas of a grandstanding excuse for manhood out of your little head, and start being the sissy you have so desired to be. Your time has arrived dear.”

“I am not sure”, evelyn squeaks.

What has happened to her voice? It is so much softer.

“Umm… can I have some time?”

“More time?” laughs Jill. “Your time is now honey, everything is in order and you have already signed away the consent form with your marriage certificate years ago. Let it go dear, We are here to help you.”

“Now, what does sissy want?”

“sissy wants to be taught how to serve”

“Now.. wasn’t that easy? Didn’t it feel right?”

“Yes mam, it feels right.” evelyn’s voice is soft and sexy.

“You will be of real use now to your Mistress and to anyone she may wish to share you with.”


After what seems hours, she again sleeps, awakens, each day or what is passing for days seems to continue, time has lost if reference.

She is once again in the virtual reality unit. As Pico helped her get dressed she could feel her plug pulsing, he has it set to a remote and can control it at will. Evelyn is excited! She drinks the elixir eagerly and is lost in a hypnotic semi-conscious dream.

Her Mistress is there in her dream. She has not seen Joyce in…well she doesn’t really know how long she has even been in this place, but she is here now, in her mind, in her memories. “Now sissy-evelyn”, her Mistress is saying, “in order for us to let your full girlishness out we need to go through all of your memories and re-write them, even to the ideas and words used before you were born. When your mother and father were speaking of you before you were born, know they always were referring to their little girl, their daughter, always it was she, sissy evelyn, to your teachers and boyfriends, girlfriends and even us together. All references to he and drew are gone. Only evelyn remains, only sissy evelyn, sweet sissy evelyn.”  The sounds, and lights flashed, rapid colors, words from memories, rewrite, erased, remade evelyn is being born.


evelyn awakens, Pico caresses her hair, she smiles. She slowly comes to recall she is at this place, she was shopping, for some cloths when Jill walks in.

“Well, now that we have some breasts upon you we can size you for your bra.”

My breasts evelyn thinks? She looks down, there on her chest are two large full, firm breasts, she looks up at Pico, he smiles, her nipples harden and she feels a slight pulse in her plug.

“Yes, Mam, thank you”, she replies with a small curtsy and smile.

The End

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i would like to take a minute of your time to thank you for your Sissify web site. Closet queens like myself have a real meeting place for information, meeting other sissies and accurate information as it pertains to sissydom.… Read more “enrietta”

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victoria nicole

wish that could happen to me


We hope the story is continued very soon .Love PrisseXXX


sissy michelle thinks “transformation of evelyn” is such an enticing story! she hopes there is much more to this story!

sissy katey

To be continued……. please please do!! …..


I need to go back in time to find myself.


Oh Pavo now I know what a sissy shemale needs . I always realized why my Anti dresses ? me as a girl ? and trained me how a girl ? should behave. From my ballet classes to hair and makeup ? I felt great. That was my reality. Now I know why I feel so feminine. A sissy.


Ummm…this sissy LOVES this story. So well written and so well thought out. Amazing! This sissy probably will read this again, and again…


If only every encounter at the clothing store went that well.


sissyroberta really loved this story s/he could picture he/r self in Evelyn’s place and this sent a lovely warm and fuzzy feeling right through sissy’s body and mind, thankyou so much xxx sissyroberta xxx


sissy loves this story, sissy so wants to read the next part.