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Chapter 1
It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself, fatalistically, swallowing hard. At least, see what happens, give it a go. It’s an exercise in building character. Yes, that’s it, life experience, he told himself. He swallowed hard as he walked up to the door, all too aware that this was the last time he would walk in such a manner. A huge change to his life lay on the other side of that door.
He had an image in his mind of himself as he was now, as the man he was about to leave behind. Nothing exceptional, dressed conservatively but with an inner life that had dominated and tormented him for so long…
He forced the image out of his mind as he reached up to touch the doorbell now in front of him. He hesitated for one last second then rang the bell. He could hear it ringing on the other side of the door but far away as if in a dream. His heart beat harder and faster than ever as time seemed to slow down. Everything seemed to be happening in slow motion. He stood there. Three minutes passed, at least. Maybe it wasn’t going to happen, maybe it had been called off, maybe… His heart leapt again as he suddenly heard steps making their way to the door. The handle turned, slowly, loudly, and the door swung open.
”Yes?” said the man on the other side.
The visitor had a glimpse of a handsome face with a sardonic smile on it before he lowered his eyes to the man’s chest and managed to utter the phrase he had been instructed to speak.
“Good afternoon Sir. I’m here to clean the house”

The man opened the door and stood aside.

Taking one last swallow, the guest entered, walking into the foyer as his host closed the door, shutting out the outside world with a soft but final sound of wood and rubber.

”Put your bag down and stand there,” he ordered, forgoing the pleasantries in a way that set the tone immediately. The guest stood on the spot as ordered.

”Well...?

The guest stood there, hesitantly.

”Off with those clothes.”

The guest took a gulp before his final dive in, and reached for the bottom of the pullover but he was stopped by the man saying, ”Uh, excuse me.”

The guest stared back. .

”Do you have something to say?”

A wave of shame washed over him. He was still in male clothes after all. He was still a man, an equal, at least up to this point, wasn’t he?

”Sir...he mumbled defeatedly, looking down again, “Yes Sir.”

Recognizing the profound and wonderful difficulty this probably took to say, the Master let the mumble slide and smirked again. The guest put his hands back down. He grabbed the pullover and raised it above his head and off. Then the shirt, then pants, then the shoes, (he had been told not to wear socks) as he stripped down for the first time for another man. Finally he stood there before the Master in a full set of women’s lingerie contrasting with his white skin. Black satin panties. Black push-up bra. Long black nylons attached to a black satin garter belt, with a little pink rose on the front. And a black choker around his neck which his turtleneck once covered. There he stood in shame and mortification, as the sissy he knew he was and had always been. The Master was now smiling, pleased with what he saw.

”Very nice.”

The sissy stood there, completely on display, knees trembling from nerves and the
novelty of it all.

”You are a real sissy, aren’t you?”

”Sir,” he whispered, “yes Sir.”

”Nice bra. Where’d you get it?

”Sir, it was my ex-girlfriend’s, Sir.”

There was a silence as the Master smiled, albeit bemused.

”You stole it from her?”
“Sir, yes Sir.”

”Where’d you get the garter belt?”

”Sir, a department store, Sir.”

”You went in there and bought it yourself?”

“Sir, yes Sir.”

”Pretending it was for your girlfriend.”

”Sir, yes Sir.”

”But it wasn’t for your girlfriend was it?”

”Sir, no Sir.”

Another pause.

”Are you glad you’re here, sissy?”

”Sir, yes Sir.”

”Are you nervous?”

”Sir, yes Sir.”

”But you’re ready to be my maid.”

”Sir, yes Sir.”

”Say it,” he said, now warmed up. “All of it.”

The sissy, while reeling from the humiliation, aware of the chill of the air conditioning against his skin, was nevertheless falling into the rhythm of the questioning. He spoke up a bit, his voice echoing in the foyer.

”Sir, I’m ready to be your maid, sir”

”Say it again.”

”Sir, I’m ready to be your maid, sir”

”Ask me for it.”

A pause.

”Sir, may I please be your maid, Sir?”

”What’s that?”

He swallowed again.

”Sir, may I please be your maid, Sir?”

There was a brief silence as the Master smiled, satisfied.

”Sissy, I want you to go upstairs. Up there you’ll find your room, on the
right. Take your bag, and leave your clothes here. Go put on what’s on the
hanger, the accessories on the night table, everything you see laid out.”

He paused, waiting.

”Sir, yes Sir.”

”Then put on your makeup and wig. You will do a good job on your makeup
won’t you?”

”Sir, yes Sir.”

”Go ahead, sissy,” he ordered, with an air of doing him a favour.

”Sir, yes Sir,” replied the sissy, as he turned and marched up the staircase in his black lingerie.

At the top, he stopped in front of the first door. Turning the knob and pushing, he saw what he both dreaded and expected inside the plain guest bedroom: a classic, black French maid’s dress displayed on a hanger, its lines forming the shape of a demure but shapely woman even as it hung there empty. While the uniform was classic, it was far from ordinary, made with customized quality and an exaggerated femininity rarely seen outside the movies, or at least movie parodies. Short flared skirt, dramatic puffed
sleeves, and white lace trimming every conceivable edge. He went and took it off the hanger. Unzipping it, he put it on the floor and stepped in, pulling it up and zipping it. It fit snugly, and intentionally so. The short skirt flared out in all directions, the square collar was edged in flounces of lace. He couldn’t help but turn a bit and watch the skirt billow. Turning to the dresser, he saw a pile of lace and ornaments, and a strange black item. He realized what it was and the dress was off again as, for the first time, he worked himself into a tight, black corset.

He had difficulty in tightening it but with each pull on the strings behind his back he felt his excitement; his shape was changing and he felt like he was becoming a new person. When it was finally on and the strings tied round, he felt that his waist was compressed by nearly four inches which forced him to take short, quick breaths. Once the dress was back on, it was accessory time. In what would have made a great movie montage sequence, he put one thing on after another in a flurry of white lace and ribbons. When this was completed, he went to the vanity and unzipped his bag. Two more items he found beside the dresser....

Twent-five minutes later, a sissy maid emerged from the room. Taking small uncertain steps in her six inch black patent heels with straps encircling each ankle, she carefully stepped out to start her slow descent down the curving staircase. This was it, her coming out party, a sort of perverse debutante ball, one with neither the high society dignity or the inevitable rich-girl-marries-and-never-has-to-work-again happy ending. The Master, hearing the stairs creak, came out to observe the spectacle unfold. Now she was descending, with smoky, heavily made up eyes, lashes lacquered in coat after coat of mascara, thick foundation and powder giving the illusion of a smooth, porcelain like complexion, and lips drawn and painted into a scarlet bow. Gold clip hoop earrings dangled against her rose tinged cheeks with each step. Down below, her dress was now accentuated with the lacy, frilly white satin apron tied into a big bow at the rear and complemented by a pair of three-inch wide lace cuffs on each wrist. Her skirt now stood out nearly horizontally below her waist, buoyed by yards of short ruffled petticoats. Her chin was tickled slightly by a white lace choker collar with a black bow. A delicate lace headband fanned out ridiculously, perched almost proudly atop her wig. A lacey white leg garter with a small black bow constantly revealed itself on her left leg as her skirt bounced exuberantly with each step. Finally, after what seemed an eternity, she reached the bottom.


”Come here,” ordered the Master, pointing to a position just in front of him

The sissy spoke even more softly now, simply unable to comprehend how this
all had happened.

”Sir, yes Sir.”

She clacked over the hard floor in her heels, taking very small steps and one foot placed directly in front of the other in what she hoped was a new and feminine gait, to the spot in front of her Master. If there was ever any doubt who was in charge before, a simple snapshot of the moment would have made it clear even to a caveman what the dynamic was now.

She stood in front of the Master for a full minute as the Master examined her. Finally he spoke.

“The corset will eventually be much tighter but not bad for a first attempt.”

“Sir, thank you, Sir”, she replied.

”Tell me, sissy, do you like this outfit?”

”Sir, yes Sir.”

”Tell me.”

”Sir, I like my outfit, Sir.”

”Then thank me for allowing you to pay for it.”

”Sir, thank you for allowing me to pay for the outfit, Sir.”

”Tell me how much you like wearing this.”

“Sir, I like wearing this more than anything else I’ve ever worn, Sir.”

”I want you to walk over to the mirror. Tell me what you see.” He pointed to a mirror on the wall. The sissy clacked over and stood in front of it, gazing at her image. If there was a trace of maleness left, it was not evident in his reflection.

”I see a highly effeminate, sissified, pansy French maid.”

”Excuse me?”

She paused for a moment, then remembered. “Sir, I see, a highly effeminate, sissified, pansy French maid, Sir.”

”Does she appear to be obedient and submissive?

“Sir, yes Sir.”

“Say the whole thing.”

“Sir, she appears to be an effeminate, highly obedient and submissive, sissified, pansy French maid, Sir.”

“Turn around. Twirl. Keep looking at yourself.”

“Sir, yes, Sir,” she said, twirling around, then whipping her head around to see herself again, now sinking down into the essence of her femininity.

”Again.”

She sank lower in her mind.

”Let your wrists hang limp. Again.”

Lower.

”Now curtsey”. She hit rock bottom.

Sliding one foot behind the other, she grasped the edges of her skirt between her thumb and forefinger. She spread them apart and bent down, bowing in the mirror. Then came up.

“Now, sissy, I can tell you that you may now love the way you look, love the uniform that you are wearing – but you will come to curse it, and wish for something more practical. But you have chosen this uniform as your working clothes, have you not?”

“Sir, yes, I chose this uniform as my working clothes, Sir.”

“I fear you did not think this through, sissy. But I gave you the choice, you made it, and now you must live with it, even when your legs ache from wearing those heels all day, even when you are on your knees scrubbing floors and still have to maintain a perfect uniform.”

The sissy’s chest heaved in her corset as the implication of what the Master said sank in. Already the heels were hurting her, as was the corset – she felt its bite.

”Come here.”

She clacked over in her pointed heels once again and stopped before him.

”Sissy, are you ready to take on your designated role now?”

”Sir, yes Sir.”

”To accept your destiny and give up your masculinity completely?”

”Sir, yes Sir.”

”To do anything and everything I say no matter how trivial or degrading, or risk being put out of the house exactly as you are now?”

”Sir, yes Sir.”

”Are you ready for your instructions?”

She stood there, swaying in her heels, swimming helplessly in her satin and lace uniform. Their roles were as black and white as the confection she now paraded in before him.

”Sir,” she replied, “yes Sir.”

Chapter 2

The Master was speaking. The sissy stood before him in the foyer in full French maid’s regalia, keeping her back straight, attempting not to sway too much in her high heels. Her palms were sweating and there seemed to be a nearly deafening silent buzzing sensation in her ears. From somewhere in the distance, she almost felt she could hear a jilted ex-girlfriend’s vaguely hysterical laughter aimed at her. Trying to put the thought out of her mind, she concentrated on the instructions now being delivered to her.

“I expect you have given yourself a feminine name which you assume is your identity. If you have done so then I have no desire to know it. To me you are simply ‘sissy’. That is your name and your title and your essence as far as I am concerned.”

“Sir, yes, I understand, Sir.”

”You are here for two things - to take care of the house, and to please me. Often, they will be one and the same. Often you will be called on to please me sexually. You will do this without any thought of your own pleasure. You will live here, but since you so graciously decided to accept my generous offer of working here for free, you are also an employee. As such, you will be expected to follow certain rules and prescribed behaviors as set out by your employer, in order to remind you constantly of your position here. Is that understood, sissy?”

“Sir, yes Sir.”

”As such, the first rule is that you will never speak unless spoken to, unless you have a question regarding pleasing me. Is that clear, sissy?”

”Sir, yes Sir.”

”If you must use the bathroom, if I am here, you must first ask me for permission. And of course, you will always go the way a proper sissy should. Do you know what that is, sissy?”

“Sir, I think so, Sir.”

”And what is that?”

“Sir, sitting down, Sir?”

“Very good, sissy. Every time I enter a room, or you enter a room where I am, or I dismiss you from a room, you will perform a deep, gracious curtsey for me. When you are standing or kneeling at attention, in other words, awaiting my orders, your hands will always be kept crossed over your apron. Is that understood, sissy?”

“Sir, yes Sir,” she replied. After a brief pause, she quickly and ditzily crossed her hands in the manner described.

”Your walk is already very feminine. That is good. Have you practiced this walk before, sissy?” There was a slight silence as the sissy looked at the ground.

”Sissy?” he raised his voice slightly.

”Sir, yes Sir.”

”Very good. But just to make sure you remember exactly who you are, when you walk, assuming they are not performing a task for me, I want your arms to be up always, and your wrists to hang limply down, fingers pointing towards the floor. I’ll bet you can do that, can’t you, sissy?”

“Sir, yes Sir.”

“Do it.”

She raised her arms to her sides.

”Do it walking, sissy bitch.”

Taking a deep breath at the sting of the words, she gathered herself and began walking towards the opposite wall her arms held up, hands dangling like a skipping little girl or a flamboyantly gay man. She turned on her heels and strode back to her Master in the same manner.

”Good sissy. Now, here’s the tricky part. Whenever I say ‘Mince, sissy,”’ I want you to walk with your hands down, below your apron, fingers pointed outward. When I say ‘Prance, sissy,” I want your arms back up like they were before. Quickly and silently. Is that clear, sissy?”

“Sir, yes Sir.”

“Are you sure, sissy?”

“Sir, yes Sir,” she repeated.

”Good. Why don’t you give it a try. You do want to try it don’t you?”

“Sir, yes Sir.”

”Let’s go. Mince, sissy.”

Keeping her arms down straight at her sides, she began the same walk again, only this time with her arms straight down, fingers pointed outward, in a manner befitting some sort of walking Barbie doll.

”Prance, sissy.”

As she got to the end, she suddenly lifted her arms up. Turning, she held them up as her hands flopped from side to side.

”Mince, sissy.”

Back down went the hands, the arms swinging stiffly back and forth.

”Prance, sissy.”

Again with the dangling wrists.

After a few passes, the Master ordered the sissy to stop, barely concealing his mirth at this game. She came to a halt before him, her bosom now appearing to heave under her bodice in deep gasping breaths.

”Very good sissy. I want you to understand perfectly clearly. From now on, you are to do everything as told. If I order you to lisp, you will lisp. If I order you to speak in a French accent, you will do so. If I have to lift a finger I do not want to lift, or utter an instruction I do not want to have to utter, you will have failed, and therefore be punished, or cast out the door as dressed. You don’t want either of those to happen now do you, sissy?”

”Sir, no Sir.”

“One more thing, sissy. You are to be a sissy at all times. If I catch the slightest glimpse of masculine behaviour in the way you walk or talk or behave, then you will be punished severely. Remember you are a sissy, a pansy, a fairy, a faggot and you must show this at all times. A sissy is not a woman so you will not act like a woman but as a sissy. That is why you prance and mince; that is why you wear clothes that no woman would wear. That is why you will have to adapt to walking in those ridiculously high heels for the entire day. Do you understand, sissy?’

“Yes, sir. I do understand, Sir,” she said, pitching her voice higher than usual.

”Good. Since you will be adopting the role of the woman of the house, I think it is only appropriate that you have a tour, don’t you?”

“Sir, yes Sir.”

”Prance, sissy.”

Turning his back, he headed toward the stairs. With wrists limp and heels clacking behind to keep up, she followed him up the stairs. He went to the room where she had changed.

”This is your room, where you will sleep and dress. You may repair to it only at night, or when I say you may. Is this clear, sissy?”

“Sir, yes Sir.”

”I will be making some minor modifications to it later, but you needn’t be concerned about that. Let’s keep going. Mince, sissy.”

Lowering her arms to the straightened position, she followed along.

”Here is the Master bedroom. You will not enter hear except to make my bed in the morning, or when I call you. Is that understood?”

“Sir, yes Sir.”

”Prance sissy,” he snapped, turning again to show her the guest bedroom. While there was no one staying there, she would still be expected to dust and vacuum each day, freshening the sheets once a week, hospital corners on the sheets always. (Mince, sissy.) This applied to all rooms of the house, the dusting and vacuuming. He showed her to the laundry room, where she would be doing all his laundry, “Except my underwear, which you will personally wash by hand, and your own clothes which will are far too fine and delicate to go through the washing machine.”

(Prance, sissy) “Sir, yes Sir.”

After showing her all the relevant areas of the house and giving her instructions on opening and closing the blinds, the lights, the garbage (mince sissy), etc., the tour concluded in the kitchen. (Heel sissy.)

”Finally, one of the most important rooms in the house for you sissy. Here, you will be cooking all of my meals, and cooking them well. But I’m certain that with the right incentives you will learn to become a very adequate, if not a gourmet chef in no time at all. Except tonight, since we got a late start, and you have a big day ahead of you tomorrow. I will order food and you can fix yourself a salad. At any rate, you will keep the place immaculate, the dishes dry and sparkling, and the floors waxed and shined every day so I can see my reflection. I’m afraid I’ve let the place go of late, but that doesn’t matter now. In fact, it won’t matter ever again, will it, sissy?”

”Sir, no Sir.”

”You do know how to wax a floor so I can see my reflection in it, don’t you, sissy?”

“Sir, yes Sir.”

He stood there watching her.

”Well what are you waiting for?” he said, enjoying her mouth suddenly drop open in realization.

”Get to it!”

”Sir, yes Sir!” she replied, scurrying off to the cupboard to retrieve her cleaning supplies.

Chapter 3

After she had scoured all the dishes, given the kitchen a thorough cleaning and finished waxing the floors, sissy was set about the house to do a thorough vacuuming and dusting while Master did some work upstairs. Quietly and demurely, she scampered about in her maid’s uniform with a pink feather duster she herself had bought, holding it between her thumb and two forefingers as she dusted the place up and down.

”Don’t forget the blinds, sissy!” Master yelled down, as he set about hammering or drilling or some other manly art that was far beyond the capabilities of what this sissy could do, at least without chipping a nail or putting a run in her silk stockings. As she did the windows, she wondered if any passersby could see her, but then realized with a start that it was probably a bit too late to preserve any dignity now.

By the time she had finished her work and had the place sparkling, it was approaching early evening. This meant it was time to set the dinner table. Carefully she laid out the place setting, complete with white linen tablecloth, silverware, a napkin in a ring, lit candles, the works. It was a lavish affair straight out of an old movie, with the exception that the table was only set for one. After seating her Master and curtseying, she brought out a simple but elegant pasta dish that she had prepared herself. During dinner, she was required to stand to the side, refilling Master’s water glass whenever it was below three quarters full, and his wine glass if he wanted, which he signaled by tapping once on the glass with a spoon. When it was finished, Master signified his approval.

”Not bad for a first effort, sissy, but I believe in time you will learn to do even better, becoming a real gourmet cook as well as a maid. Of course I know you were limited in the ingredients you could use, but you’ll rectify that when you go shopping.”

Sissy felt her knees go weak at this thought.

”Oh don’t worry, you can have the food delivered for now, of course. We don’t want you to take any time away from your housework. If you’re lucky, I may even entrust you with the responsibility of signing for the delivery. How does that sound, sissy?”

“Sir, very good Sir,” she swallowed

”Good. Now clean up.”

Sissy curtseyed as the Master got up and left, then removed the silverware, plates, and the tablecloth, all of which were to be washed. Once she finished with this, she was allowed to have dinner herself: a small salad with cucumbers, shredded carrots, sprouts for protein, 4 croutons, and no dressing. In spite of the meagerness of her supper she was by now starving and relished each bite as if it were a porterhouse steak.

After she had finished cleaning up, Master summoned from the living room. She minced out and curtseyed deeply.

“Fetch me a drink, sissy.”-

“Sir, yes Sir.”

She curtseyed again and disappeared into the kitchen. When she returned, she was carrying a silver tray. She set it down beside him. From a small tumbler, she reached in with a pair of silver tongs and withdrew several ice cubes, dropping them in the glass. Then she began to open the can of Coke. She could feel his amusement as she struggled with the tab while wearing the long, maroon, square-tipped press-on nails which she had been ordered to put on. Finally she popped it open and poured it in, handing it to her Master.

”Thank you, sissy. How are your feet, sissy?”

“Sir, a bit sore, Sir.”

“Why don’t you kneel for a bit,” he said, pointing down at his feet. “After all, we don’t want achy feet do we?”

“Sir, no Sir,” she replied, kneeling at his feet.

”Take off my shoes,” he commanded. She began to untie his laces, but he stopped her.

“Always kiss my shoes before you touch them. Got that sissy?” She replied instinctively, by leaning forward to plant a kiss on the toe of each shoe.

”Very good, sissy.”

She then untied his shoes and removed them one by one, placing them to the side. Then the socks, which she was folded neatly and put to the side as well.

“I’m going to allow you to rub my feet sissy. Aren’t you honored?”

“Sir, yes Sir.”

”In fact, I think you should always ask to rub my feet after dinner, or whenever I return home. Doesn’t that sound like something a good little maid should do?”

“Sir, yes Sir.”

”Well?”

“Sir, may I please rub your feet Sir?”

“You may.”

Sissy proceeded to give a long, sensuous foot massage. He lay back as she rubbed and kneaded his feet on her knees. About five minutes or relaxation, he seemed to think of something and sat up for a second. Reaching down, he picked up one of his socks. Unfolding it, he put it to sissy’s lips. Confused, she puckered up to kiss it, but instead he began stuffing it into her mouth with his finger. Her eyes went wide as she tasted his toe jam and foot sweat, but continued rubbing as he sat back again, satisfied and smiling. After over an hour of this, he removed the sock.

”Stand up, sissy. I think it is time for both of us to get ready for bed. I’m taking it easy on you tonight, but you’ve got a big day ahead tomorrow.”

”Sir, yes Sir.”

Master had removed her bedroom and bathroom doors, now allowing her to be seen at all times. She was permitted to remove her uniform, sleeping in full lingerie with a flimsy, see through, ruffled babydoll nightgown. Beside her bed was an electric bell, which she would answer if Master were to need anything during the night. After turning down the Master’s bed, fluffing his pillow, and making sure Master had everything he needed, she was allowed to lock the front door, turn out all the downstairs lights, and go to bed. She tossed and turned for a bit, not used to her new sleepwear, but within fifteen minutes she was sleeping like a little girl after a full day of play, dreaming that this might happen to her...




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I have been submissive for as long as I can remember. Growing up I adored my mother and would watch everything she did around the house. Eventually I would help her with more and of the cleaning, cooking and laundry. She playfully called me her maid when I was helping her and I began to refer to her as Ma'am. When I was 13, we decided that I should go to a friend's Halloween party as a French Maid. For some reason this really excited me! My first masturbation fantasy was imagining...

3 years ago
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The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

4 years ago
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Sissy Maid

I was just out of high school working at a convenience store. Two of my regulars were a nice gay couple, both were a little feminine but one was definatley fem always wearing pink shirts and revealing shorts in the warm months. One night while I was talking with my friend about coming up with the money to buy my girlfriend an expensive gift they came in and where listening to the conversation. After my friend left the more feminine one named Toni came back.He said I could not help hearing you...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

3 years ago
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My roommate new sissy maid

I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me” I have no choice she is more stronger than me “whatever you say” I put the outfit and a chastity cage on and when I started working she...

Interracial
2 years ago
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New GF Trains Me to be a Sissy Slut

"That's it baby! You are such an amazing cock sucker!" I moan around the cock in my mouth as I bob up and down quickly. I feel hands on the back of head grab my hair to stop me from moving up and down the amazing 10 inch black cock. I've been kneeling for almost twenty minutes slowly working this monster. I've only been able to take just over half of the cock so far. "You are doing very well sucking your first dick. Though a good cock whore needs to learn to deepthroat and feel what it's like...

3 years ago
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Newhart The Made Maid

"Stephanie, I never said you weren't pretty. I just said that some men prefer, well, different types of women." Joanna grunted as she lifted a sack of potatoes from the car. "You can't expect every man to drool over you." Stephanie continued to sort through the brown grocery bags, searching for the one with lightest load. "And why not, Joanna? You don't really expect me to believe those boys were looking at you in THAT way, do you?" Joanna, a tall, slim woman of about 40, pushed a...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

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