My top ten transgender story

Samuel Nevada had a secret. A secret so hidden even he didn’t know about it. But that’s getting ahead of the story.

Sam had just finished the last of his finals in his Law classes and with only one year left before he could take his BAR had decided to celebrate by bar hopping that night. Dressed in his best “cruisin'” clothes he had gone from bar to bar, looking for a woman to take home and fuck. Usually, he didn’t have a problem with it, but tonight, all the women seemed resistant to his best advances.

He had made it to a strange bar on the far side of town and was about to go home when he saw her, a tall (at 6′, she stood 4″ over him), statuesque brunette with big tits (easily a D cup) and a figure to match. He walked over to her. “Hey, babe, come here often?”

She turned to him and gave him an inquisitive look. “Often enough. Why?”

“Well, I was just wondering what your plans for the night were.”

She looked him up and down. “Oh, I don’t know. Find some guy, take him home, ply him with drinks and then have long, satisfying sex. Interested?”

Sam was shocked and intrigued. Never had he found a woman so forward and open about sex. Most seemed content to just let him take the lead. This one seemed strangely… refreshing. He extended his arm to the lady. “With a woman as beautiful as you? Most certainly.”

The woman took his arm and started leading him outside. “I’ll drive.” Sam was flabbergasted, but allowed himself to be lead outside. The woman walked him to an expensive sports car that must have cost her easily in the $40-50,000 range, making Sam glad that they hadn’t returned to his own used car.

The woman opened the passenger door for him. Despite the strangeness of it, Sam allowed her to help him into the car. She closed the door behind him, then got in on the driver’s side.

“Wait a minute,” he said, “what about my car?”

She gave him a smile that melted him inside. “We can come back for that later.” Sam could only nod as she pulled out.

They drove in silence out to the richest part of town. When Sam noticed where they were going, he was glad that they had not gone back for his car. This part of town was fenced in and patrolled by rent-a-cops. Even if he could’ve managed to get in, he probably would’ve been followed by some security guard for every inch of the drive.

They pulled up in front of a mansion. Sam sat in stunned silence at the size of the house as the woman got out and opened the door. “Nice place,” he murmured as she led him up the front steps of the house.

“Why, thank you,” she replied.

They went inside and into a parlor. “Have a seat while I make us some drinks,” she said.

Sam sat down on a couch as she went over to a bar and mixed some drinks. While she worked, he looked around. Everything in the house bespoke wealth. Every stick of furniture was an antique; the rugs, even the drapes were a rich tapestry of silk. He was still ogling the place when the woman returned with the drinks.

It had a strange greenish color and Sam sniffed at it. “Mmmm. Creme de Menthe.”

“Drink up,” she said as she drained her own drink.

Sam shrugged and drained his drink. The woman sat beside him on the couch and started rubbing his crotch. “Tell me something,” she said.

“Anything.”

“Do you think I’m pretty?”

“Very.”

“Do you like my tits?”

“Oh, yeah.”

“Would you like a pair of your own?”

“I… huh?”

“Would you like a pair of your own?”

“What’re you talking about?” Sam noticed an itching in his chest and reached up to scratch it. As he did so he saw that his shirt was starting to tent away from his chest. He watched in fascination as he actually grew tits. He seemed stunned until his shirt burst open, exposing two mammaries easily as large as the woman’s. “Oh, my god!” Then Sam noticed it. “My voice! It’s so high! What did you do to it? What did you do to me?” Sam grabbed his crotch and breathed a sigh of relief. The seat of his manhood was sill there.

“I’ve made you into my little play toy. And if you want to be returned to normal then you will obey me implicitly. Come with me.” She got up and left the room.

Unable to do anything but comply, Sam got up and followed. They went upstairs and into a very effeminately decorated room. “This,” she said, “will be your room while you are here as my girl.”

“And how long will that be?”

“Well if you could pay the reversal fee, you could make the return to manhood tonight.”

“How much is it?”

“A quarter of a million.”

“Dollars?!”

“No, pesos. Yes, dollars.”

“Please, have mercy. I’m just a poor college student.”

“Well, if you can’t afford it this year, how do you expect to afford it next year?”

“Next year?”

“Yes. You’ll need a dose every year to prevent your body from returning to this state. Further, if you don’t get the reversal agent or at least a delaying agent every 24 hours, this becomes permanent.”

“Permanent?!” Sam squeaked. “Why are you doing this to me?”

“Well, I go out every once in a while and find some sexist pig and transform him into my she-male toy.”

“Sexist pig? I’m no sexist pig. What are you? Some man-hater that thinks that all men are pigs?”

She gave him an inquisitive look. “Perhaps you’re right. Perhaps I have misjudged you. Tell me the truth now, and you may get the reversal agent for free for the rest of your life.”

“Okay.”

“Were you prepared to have sex with me tonight?”

“Truthfully, yes.”

“Okay, then if you can do just one thing for me, you’ll have earned those free dosages for life.”

“Anything.”

“Just tell me my name.” Sam stammered for a bit, before she said, “Mm-hmm. You were prepared to go to bed with a woman whose name you didn’t even know, just because she looked like this.” The woman waved her hands down her body to make her point.

“Yeah, well, what’s my name?”

“Samuel Nevada. One year away from getting his Law degree from the local state college. Has maintained a grade point average of at least 3.5 since graduating high school. And in the last year you have had sex with 230 different women, not one of which became a relationship.” Sam was stunned. “I cull my conquests rather seriously. Now let’s get you dressed. Get out of those men’s clothes. They look silly on you.”

Sam stood there for a few seconds before she said, “Oh, come now, you can’t be shy. You were just about to expose yourself to me for sex.”

Sam shrugged and undressed. It was then that Sam got a view of some of the features of his new body. His arms and legs were now hairless. His waist seemed impossibly small in comparison to his hips (which he was sure were now wider than they were) and his bust. His feet and hands were both smaller and more delicate. And he may have been imagining it, but it somehow felt as though he ought to be standing on the balls of his feet.

The woman took the clothes and threw them into a chute in the wall marked “Waste”. She then got a tape measure out of the drawer and proceeded to measure Sam’s new body. When she was done, she said, “Your new proportions are 36-30-34. And you have a C cup. You’re a little wide in the waist, but that can be handled.”

“C cup? But my tits look as big as yours. And I’d swear those were D cups.”

“They are. But you’ve got a smaller frame than I do, both in height and around the torso. As a result your tits look bigger.”

“Oh.”

“Now we’ve got to get your waist size down. Once we’ve had you on a special diet for a couple months, you should be down to the mid-20s, but till then…” She went over to the closet and returned with a bright red, leather corset.

Sam gulped. “Do I have to wear that?”

She seemed to consider that. Finally she gave him a lustful look, like a man might give any beautiful woman. “Well, if you really want to walk around in the nude, I think I could get used to that.”

Sam blushed and took the corset from her. He stepped into it and pulled it up around his waist. The woman stepped behind him, took the corset’s laces and pulled them as tight as she could as he gasped for air under her onslaught. It wasn’t until she had tied them off that Sam realized that the laces were in that place in his back which was hardest to reach. There was no way he could get in or out of the corset without someone else’s help.

After she was finished tying him in, she went over to the small dresser. Pointing at the top drawer she said, “This drawer will contain your bras and panties.” She opened it. “You’ll notice it’s empty. You won’t be needing a bra till you no longer need a corset, the cups on the corset will provide all the support you need. And in either case you must earn the right to wear panties or a bra when not in your corset, which will not be often.”

She closed the first drawer and opened the second. Inside were some socks (all small and feminine in style) and stockings. “This drawer will contain foot coverings. Except for shoes, of course, which are kept in the closet.” She took out a pair of stockings and tossed them to him. “Put these on.”

Sam sat down and pulled the stockings on. The stockings were different from any he had felt on any woman’s legs. Further, they weren’t elastic at the top, and in order to keep them from falling back down, Sam had to secure them using the elastic straps hanging at the bottom of the corset. After he was finished, he rubbed his thighs through the stockings. “These feel really nice.”

“They should. They’re silk.”

“Silk?” Sam said, obviously impressed and feeling flattered. Then, to attempt to cover his pleasure, he said, as sarcastically as he could, “For a slave like me? I’m impressed.”

Ignoring his sarcasm, she replied, “Don’t be. I have an image to maintain, so even my lowliest slave gets the best clothes.” Continuing on, she pointed to the third drawer. “This drawer will contain blouses and the bottom one will contain skirts, and perhaps, if you’re very good, slacks. All must, of course, be earned.”

She walked over to the closet and returned with a short, red dress. “Except for your corsets, stockings and heels, this will be your only clothing until you earn more. You will remove it before bed and wash it by hand, hanging it to dry for the next day. You will not be allowed to leave this room without it on. Doing so is grounds for punishment.”

“What kind of punishment?”

“Pray you never find out.” Sam gulped. The woman returned the dress to the closet. “You should go to bed now. You will have a long day tomorrow.”

“What about this?” he said, waving his hands along the corset.

“To get you used to it, you will sleep in it. At least for a few nights.”

Sam wasn’t sure he could manage that; the corset was unbelievably tight; but being afraid to argue, all he said was, “Yes, ma’am.”

“Very good. Very polite.”

As she started to walk from the room, Sam asked, “Excuse me, but what is your name?”

“Now you ask. My name is Elaine. For the duration of your stay with me you will refer to me as Mistress or, more formally, Mistress Elaine.”

“Yes, Mistress Elaine.”

After she left, Sam noticed and went over to a full length mirror hanging on the back of the door and got a good look at his new body. Sam was stunned. Except for his hair, he was a looker! His face had taken on a rounder, more delicate appearance, and his arms and legs were both much slimmer and seemed to match his new feminine body perfectly. He did have to admit that Mistress (amazing how easily he thought of her by that title) was right. Although shapely, even in the corset, to be perfect, he could’ve stood to lose a couple inches from his waist. And as he stood there a thought came unbidden to his mind, “The red may give me a slutty look, but blue would’ve gone much better with my hair and eye color.”

Sam stopped and shook his head. “Was I just critiquing my weight and clothes like a woman? I must be more worn out from all this than I thought.” He walked over to the bed and crawled in and fell asleep.

****************

THE NEXT DAY…

Sam was awoke by a strange woman’s voice. “Good morning. Wakey-wakey.” Sam groaned, but crawled to the edge of the bed and sat up. “How’d you sleep?” she asked.

“Lousy.”

“Not unusual. It takes a while to get used to sleeping in the corset.”

“It wasn’t the corset. That didn’t bother me near as much as I thought it would. It was these strange dreams.”

“Really? What about?”

“That’s just it, I don’t remember any details, just some really disturbing feelings. Oh, I’m sorry. You probably already know, but my name’s Sam.”

The woman, a striking native American woman dressed in a dress that looked like it was from the pre-civil-war south, complete with large hoop skirt, said, “Yes, I did know, but it’s polite to introduce yourself anyways. My name is Linda, but you will refer to me as Lady Linda, or by the honorific, milady. I am the head of Mistress’s domestic staff and will control your training for your stay.”

“Yes, ma’am.”

“No, not ma’am. Only Mistress is to be referred to as ma’am. Milady.”

“Yes, milady.”

“Very good. And don’t worry about the dreams. Many of our staff had nightmares the first few nights after their transformation.”

“Well, they weren’t really nightmares, just disturbing.”

“Well, if they continue too long, then we’ll worry about it. For now let’s get you out of that corset and into a fresh one.”

“Yes, milady.”

The woman helped Sam out of his corset and got out a new one, this one blue. After Sam got into it, he caught a look at himself in the mirror. “I was right,” he thought, “blue is a better color for me.”

Linda looked through the closet and asked, “Did Mistress issue you a maid’s uniform?”

“No, just that red dress.”

“Then let’s go get you one. Follow me.” Linda walked outside the room, but when Sam didn’t follow she turned and said, “Come on.”

“No.”

Angrily, she asked, “Are you defying me?”

Sam was frightened, but, in a trembling voice, said, “Mistress said I wasn’t to leave the room unless I was wearing that dress.”

Linda smiled. “Very good, Sam. You passed your first test.” Sam breathed a sigh of relief. “Although I am in charge of your day to day life here, Mistress is always the ultimate authority. I may give you conflicting commands because I want to test you or because I haven’t been informed as to what Mistress has ordered. You are NEVER to disobey Mistress’s commands. Understand?”

“Yes, milady.”

“Further, you may be leant to others. Unless Mistress says otherwise, their commands do not override mine.”

“Yes, milady.”

Linda reentered the room. “Now let’s get you into that dress.”

As she got the dress from the closet, Sam asked, “Milady, may I ask a question?”

“Yes, you may.”

“Earlier you mentioned that other members of Mistress’s staff had gone through a transformation like mine. How many are like me? Were once men, I mean.”

“All of us.”

“All of you?”

“Yes. Mistress’s entire staff is composed of obnoxious, chauvinistic men who realized they were happier as women. Not having any legal identity, Mistress was gracious enough to put us to work on her staff.”

“Well, that’s not going to happen to me.”

As Linda helped Sam into the dress, she said, “Probably not. Not many do decide to become women.”

“Good. I was beginning… to think…” Sam stopped, not wanting to voice his concerns.

“That we were going to force you to be a woman for the rest of your natural life?” Sam nodded. “No. As soon as Mistress feels you’ve learned your lesson, or three months have passed, whichever takes longer, she’ll give you the reversal agent.”

“So I’ve got to spend at least three months like this? Even if I learn my lesson in a week? Why?”

“Your three-month servitude will repay Mistress for the costs involved in creating both the transformation and the reversal agents.”

Sam wanted to protest, but realized it would be useless. “So how is my servitude to start?”

“With breakfast.” Sam raised an inquisitive eyebrow. Linda smiled and said, “Mistress wants to speak to you, personally. You’re to serve her at breakfast, after which, she will speak to you about your duties.”

Linda got out a pair of low heels (1/2″) and gave them to Sam. After he put them on, she said, “Now come along.”

Sam followed, amazed at how comfortable he was in the heels, and how easy it was to walk in them. When he mentioned it to Linda she snorted and said, “Wait until you’ve spent all day in them and then tell me they’re comfortable. As for finding them easy to walk in…” She shrugged. “Maybe you’re just a natural.”

“That’s not funny.”

She looked back at him over her shoulder. “I wasn’t trying to be.”

They walked through the house until they reached the kitchen, where a collection of women were running about preparing food. There was a tray waiting on a counter with scrambled eggs, toast, juice, and milk on it. Linda pointed at it. “This is how Mistress likes her breakfast, when she has it, that is. You’ll find that she skips a formal breakfast as often as not to work in her lab. Notice the firmness of the eggs. Mistress doesn’t like them much firmer than this, but she detests runny eggs. The toast should be approximately this color, and she will want it buttered at the table, in front of her. After you take this out there and set it in front of her, that is what you will do. Check the juice and make sure there are no pits. All this has been done for you today, but this will be your job on later days.”

“What do I do if it doesn’t meet up to standards?”

Linda waved her hand to one of the girls in the kitchen and said, “Liz.” A blonde woman with her hair in a bun, impossibly huge tits (Sam guessed that they must’ve been somewhere around an I or J cup) and a stern look in her eye came over. She, like everybody but him, was dressed in clothes from the pre-civil-war south. “This is Lady Elizabeth. She is in charge of the kitchen. You will rarely find anything seriously out of order, but if you do inform her.”

Sam nodded. Elizabeth walked up to him, and gave him a cold, impersonal stare over her huge tits. “If Mistress ever gets imperfect food, as head of the kitchen, I get punished. But then, I will not only punish whoever prepared the food for their failure, but also you for your failure to catch it. Understand?”

“Yes, ma’am.”

Elizabeth hauled off and slapped him. Sam wondered what he had done when she said, “Address me as milady! Only Mistress is ma’am!”

Holding his face, Sam said, “Yes, milady.”

As she walked away, Linda said, “She takes her job rather seriously. Just make sure you do your job, and you won’t have any troubles with her.”

Sam watched Elizabeth walk away and despite himself, he felt attracted to this strong-willed blonde. He shook himself out of his reverie, and said, “Yes, Lady Linda.” Without being prompted, Sam picked up the tray, and said, “Is there anything else? I don’t want to keep Mistress waiting.”

Linda smiled, pleased with Sam’s initiative. She picked up a napkin and spread it over Sam’s arm. “After placing the tray in front of her, place this in her lap. Be very careful not to touch her directly unless she prompts you to do so.”

Sam nodded and Linda pointed him through another door. Sam backed through it, so as not to risk disturbing the food (as he had seen waiters do in fancy restaurants) and entered an elaborate dining room. Sitting at a huge, antique table was Mistress Elaine. He walked up and set the tray in front of her. As he spread the napkin in her lap, he said, “Good morning, ma’am.”

She neatly folded a paper she was reading and set it to one side. “Good morning, Samuel.” Sam breathed a quiet sigh of relief. He had been worried that Mistress would force him to take a feminine name, and he wasn’t sure he could deal with that. “How did you sleep?”

“I had some bad dreams, but Lady Linda assures me that that’s not unusual, and that they’ll go away in a few days.”

“If they don’t, make sure to inform me. Have a seat.”

Sam sat down in the seat nearest to her. As he watched her eat, he realized how hungry he was, but remained silent as she finished her meal. As she wiped her mouth with the napkin, he worked up the nerve to say, “Ma’am?”

“Yes, Samuel?”

“I know you mentioned that I would be on a special diet, but I’m awfully hungry, and I was wondering… Will I be allowed any breakfast, at all?”

“Of course. Starvation diets don’t work. But you will eat after I do. Linda will show you where.”

“Yes, ma’am.”

“After breakfast, my chauffeur will take you to a local beauty salon and get you fixed up. Then you will return here and Linda will instruct you in your day’s duties.”

“Yes, ma’am.”

Mistress Elaine pulled out a bottle full of something green. “This is your delaying agent. It will keep you from becoming a woman permanently, at least for the next twenty-four hours. It should be taken on an empty stomach, so drink up.”

Sam took the bottle and quickly downed it. He felt a brief tingle throughout his body. “Thank you, Mistress.”

“You’re quite welcome.” Mistress stood up, and began to leave the room. As she passed Sam, she said, “You know, you really do make a striking woman.” Sam winced a bit. Not because he hated what she had said, but because he knew she was right and, somehow, that pleased him more than he cared to admit.

After she left, Linda walked in. “Now, would you like to go to the salon, or have breakfast first?”

“Breakfast, milady.”

“As you wish. Follow me.” — “This is reality, not T.V. Can’t you tell the difference?” “Sure, I just like T.V. better.”