Blackmail by Choice

Christopher was twenty six and had gotten his degree from a prestigious university in southern California. He had worked for the best grades possible all through high school, and all through college to get his degree. It worked out because in his field he was already getting job offerings before he had graduated even. So when he did graduate, he already had a job and a plan. He moved into the silicon valley and began working as a software engineer immediately at a well established tech company. They paid pretty well for a straight out of college employee, and the benefits covered his basic needs. But what really excited him was that he could work from home.

But working from home meant nothing if he didn't have a home, and as a guy straight out of college and just starting to work, he didn't have much money. He barely found a tiny studio apartment that he could afford and stand to live in and took the offer right there. He moved what little he had in within the next few days, and prioritized setting up his desk and computer. From then on he could begin to work, and he did, which meant he never really got around to finishing the rest of his apartment. The rest laid in boxes and scattered around in a mess behind him while he worked most of the day.

Chris was by no means extraordinary, nor was he by any means unhappy. He loved his job, and he was good enough at it that his bosses never had to talk to him much for his work. His pay slowly began to build, and as he had been used to a meager living through college he didn't really spend it on much. He paid for food, bills, water, and the occasional replacement pair of shorts but outside of that he didn't really spend his money on much. So it just began to build up. He wasn't very social either, a trait that had been true all the way back to high school. He didn't leave his house often except for the necessities, and he had lost his connections to the few friends he had in college. He was truly a loner.

But he was used to it. In high school he had been one also, and same with college. He had always had a few friends to talk to and keep himself occupied but he really focused on his studies. That also meant he had never dated a girl. He had gotten close to a few, but things always broke away as they realized what little experience he had. He wasn't totally a freak, but strange would be appropriate. He had strange tendencies when around others, and didn't truly know how to handle himself. His parents had known it, and his sister had too. But when he left for college, that was the end of their involvement in his problems.

He got help paying for college from his parents for a while, but soon they let him deal with it alone. He worked, and took out loans but was smart in how he did it as to not bury his future self in debt. He still had it lingering, but it was not at all at the front of his mind. His family had loved him, but after they stopped helping him pay for school he began to drift away from them. Apart from the distant calls, they didn't talk much, and that's how Chris liked it. He liked the independence and living his own life. So the last thing they had heard at this point was that he was moving to the Silicon valley to look for work, and outside of that nothing.

But his social ineptitude was far from over with a few strange tendencies. Having never dated anyone also meant he had some pent up frustration in more ways than one. In high school porn became one of his closest friends and he tried quite a range of genres and fetishes. He experienced quite a bit in that time, but as he went off to college it began to steady out, though still persisted through his lack of dating. He was still extremely desperate for sexual experience that he began to respond to any form of it that he could find. And in the later half of his last year in college is when he remembered a fetish called 'Sissy' that could possibly help him out.

He looked deeper into the fetish which he had touched on and began to think. He wasn't initially all too into the idea of boys dressing like girls and submitting themselves to becoming sex objects, but the more he studied it the more it intrigued him. He looked into it more and more and began to interact with others on forums and chatrooms dedicated to the fetish. By the time he graduated, he had begun his pit fall into full submission to his sexual desires. And he had chosen a persona that he thought about delving into, a fully invested sissy boy named Kallie.

Chris was already very feminine. His face was hardly a perfect girl's, but it was far from manly. And his body was void of muscle and was instead very skinny. He wasn't very hairy, and everything could probably be shaped to look good. His pale white skin could probably be tanned nicely, he had never tried, and his hands and feet were pretty girly. If anything, however, his eyes were his girliest feature. Countless women and guys both had told him that his eyes were strangely beautiful, in a girly way, and that the pretty deep blue hue was like a calm ocean. He had brown hair too that was hardly describable as manly.

And now that he was living alone, under his roof and his rules, he decided to enact his plan. He began to shave his whole body, every single inch, turning him into a smooth skinned boy. He used lotion over every inch of that skin to make it softer, and he began to switch to girly soaps and shampoos which began to bring more color and life to his hair, which he had begun growing out as soon as he began to devise this plan. He had looked up countless tutorials, videos, and recommendations about workout programs to build your body into the perfect, girly shape, and he began to work on them. In fact, these workout programs were the things that got him to go to his school's gym for the very first time ever.

He began to study makeup videos online, something which he didn't get to pratice until now. He studied styles and how to dress himself to create the look for his persona he had chosen. He decided that Kallie was a fun tease, edging on the side of slutty. He envisioned her with long brunette hair, short black skirts, white clingy blouses, a decent amount of makeup, and some large hoop earrings. This he decided was her full gettup look, and otherwise he decided she was the type to wear tight jeans. And so now that he lived in his apartment, he began to practice the makeup lessons he had learned and to spend all of his excess money on clothes online. The packages would arrive on his doorstep and he would bring them inside to begin to fill the closet which had previously stood empty. All of his boy clothes were mostly in a box, or hamper.

Once enough clothes and makeup had been delivered that he could fully begin his transformation he tried it. He went for his original vision, black skirt, tight white blouse, and a good amount of makeup. He stood and looked at himself in the mirror and was unhappy with the results. There was plenty of work to be done, but as he looked over his body he did take note of the progress made. His figure was becoming very feminine, almost filling into and shaping the clothes perfectly. His makeup was good, but not fully there yet, and as he looked he figured some things that he needed to help the image.

He knew that he couldn't deal with himself to go out in public and get his ears pierced, so he had looked up many tutorials how to do it at home safely, and so he sat in front of his mirror on a box with a small sewing needle up to his ear. He dabbed the flesh with a wet paper towel and lined up the needle to where the videos had told him to do it. He braced himself, and bit his tongue through the sharp piercing pain. But to his surprise, it only lasted a moment and was soon over. He pierced the other and cleaned up the blood. An hour or so later, he had cleaned the piercings of blood and decided that he could at least try on his hoop earrings he ordered, which helped him to visualize his idea of Kallie.

After that night he kept working, but this time more motivated than before. He did double sets of the workouts, practiced his makeup over and over during the day, and spent any free time devoted to helping Kallie. He would sit through his time at work with full makeup on and his hair brushes next to him. And not even in a full three weeks, he tried again. He had more clothes this time and much more experience with all of the makeup and things he had tried. So he got fully dressed in some black tights, a white T-shirt, a pair of black lace panties and bra which he stuffed with some B-cup rubber fakes that he had bought, plenty of slutty makeup, and the hoop earrings. At this point also, Chris had ordered a pair of black 3" heels which he slipped on. He sucked at walking in them, but practice is what he needed.

So he walked up to the mirror as Kallie, and what looked back at him was just that. She looked much more convincing, in fact she looked extremely sexy in her own opinion. Her face was nearly passable, and her body was filling the clothes perfectly with a larger bum, smaller waist, and a bit of a thigh gap. Her hair was the soft brunette she had wanted, and it came down to mid-shoulder length. She spun around in the mirror, stumbling and nearly falling in her heels, and looked at every angle of herself. She loved it all, and couldn't stop looking.

She made some kissing faces, and struck some poses in the mirror, mesmerized by Kallie. She picked up her phone and took a few photos of herself, and after looking at the photos again she had a strange feeling. The feeling was similar to something she had felt while looking at the photos of sissies online, but different. It seemed more like she was excited because she was in the photo, and not fully by the idea of a sexy girly boy in front of her. This is when she noticed her 3" dick was beginning to get hard in her panties. She began to rub it out when some other ideas from those sissy forums and photos came to mind.

She immediately jumped to her computer and looked up some sex toys and lubes. She scrolled through, adding a few to her cart and thinking about what she would do with them. Her dick was dying at the ideas she was having, and with hardly touching it she felt herself clench up and come into her hand as she hit the 'Buy' button. She cleaned herself up and spent the rest of the night fully dressed. When she decided it was time to call it quits, she cleaned up and took off her clothes. All except for the panties and bra, those she kept on for her sleep.

The toys arrived two days later and she began to try them out, slowly as she was new to them. But as she investigated her sex drive more and more she began to have more and more ideas. She felt the need to share her experience, and what better place than on those same forums. She began to post photos of herself, and talk to people commenting on the photos as Kallie. The feedback she got was amazing, and sexy, and she began to play with her toys and herself while reading the comments. But as she fell further and further, she kept wanting more and more.

And so she sat one night, dressed fully as Kallie, sitting with a small metal butt plug in her rear and scrolling through the forums. She had seen so many comments about people wanting to dominate her, fuck her senselessly, and to own her that this had begun to dominate her mind. She didn't know what she was looking for, but she knew that she would find it. And after some digging through multiple sites, she found it. A chat area for sissies to meet doms and to discuss with each other. And then she began to devise the next phase in her plan.

She made a post, looking for someone to dominate her. She suggested that they meet up first before any real exchange of information, but she said that she wanted someone to 'blackmail' her into being their personal sissy. She would give them her address, her job, and any contacts that might be blackmail worthy she had. And as she read over the post, she began to worry if she was making a bad decision while hitting send. The post went up painlessly, and now it was time to wait. She got many responses, often from people outside of her area wishing that they lived closer. But soon she got a response from someone who lived nearby.

She looked into them and their name was Tyrel Wilms. A 6'2" African American man who worked in law and was single. That's all his profile really said about him, outside the fact that he lived in the same area as Kallie did. She decided to look into it, and she contacted him. They talked a bit, but he was very forward with what he wanted. He asked her where they were going to meet up, and Kallie suggested a bar. Tyrel accepted her offer and they agreed to go tomorrow night. Kallie was giddy in her seat from the idea. So she marked the date in her mind.

The next day she spent working, as always, but she also spent time preparing her outfit. Once she got off work, she immediately began to get dressed. She chose a single piece tight black dress with two straps that went over her shoulders and came down to her mid-thigh. She had her black bra under it, with her B-cup fakes, and her black panties beneath concealing her tiny dick. She wore black tights and her black heels. Her makeup was extra slutty, and her hoop earrings perfected the look. In the mirror, Kallie was the perfect night crawler.

She got her things together in the small black purse that she had ordered and threw it over her shoulder. She packed the same firetruck red lipstick in it that she was wearing, and a condom in case. She counted down the minutes before she should leave, and when she got to zero she left. She had no car so she walked to the bar. It was late out, but there was still foot traffic. She kept her head down in embarrassment, but from the looks she was getting she couldn't tell if she was passing or not. As she turned down the road of the bar, she passed by a group of men standing and smoking, and when one of them whistled at her she could tell that she was passing.

She walked into the bar and walked to a table. The bar was a nice place, and one that she had read online was open to all forms of sexuality. The place was nice and clean, the music playing loud and the lights were down low. The dance floor was a little off from her, separated from the tables and the bar. The tables were the kind that stood taller with tall black leather seats. She sat and waited for Tyrel. After some time, the waitress came up and asked her for her name. Kallie was a little weirded out by the request, but gave the woman her name anyway.

The woman disappeared, and after a moment she replied with a drink. Kallie accepted the glass of scotch and thanked the woman. The woman said, "Courtesy of the man at the end of the bar."

Kallie looked up and towards the bar. At the end stood a black man leaning against the seat looking at her with a smile. When her eyes met his, she smiled, and he shifted forward to start walking towards her. The man walked up and asked, "Is this seat taken?"

"Yes, in fact, it's reserved for my date."

"That's funny actually. Because I've been here waiting for my date. She's supposed to be a beautiful young girl with blue eyes and brunette hair."

"Oh, how funny. Just like myself." She laughed.

Tyrel laughed too and sat in the black chair. He said, "Sorry I didn't come over sooner, when you came in I was in denial. You look so convincing that I was fooled and thought you were a real girl."

She laughed again, "Thanks. But that means you didn't expect me to look good?" She shot a mischievous look at him.

"Well, in my defense I've done this a couple times before, and often they don't look as good as you." He said, looking her up and down, "In fact you're definitely the best looking 'girl' I've seen." He said with obvious attention to the word, "Girl."

And so they began to talk. The ice had been broken, and for the next hour and a half they chewed their gums absently. Both of them were en wrapped in the conversation, and Kallie was lost in his eyes. They threw back several drinks each and the laughing grew louder and from deeper in the heart. Kallie couldn't help but be impressed, she didn't know what to expect of Tyrel but this wasn't it. Realistically, she expected some creep to respond to her that would be really uncomfortable and forward. But Tyrel was everything except that. He was charming, funny, relaxed, and showed no signs of being uncomfortably forward.

They finished up the last few minutes of talking by finally discussing the pressing matter. Tyrel asked, "So, by that post you made it looks like you want someone to lead your life?"

Kallie had almost forgotten that this was all from her sex driven post on the sissy forum, "Oh, yeah, I guess." She laughed, "Really I didn't know what I wanted, but that felt like it would be nice." She knew he had used a more appropriate way to describe by saying someone who, 'lead's' her life and she knew they both understood what she had asked for.

"So you said you had a job. I assume that you don't want to jeopardize it, though." He asked.

"Of course not. But I guess, that's also a part of the idea of the 'blackmail.'" She said with air quotes around the last word.

He nodded, "Ah. Well, I guess now is the part where I offer you what I can in regards to that." She sat up, knowing it was time to get serious, "Kallie. If you'll let me, I can be the one to 'lead' you. I am a professional who easily makes enough to support both of us, but I understand you want to keep your job. I also know you have some people you don't want to learn about this. So here's your offer, you be my girl and do what I ask when I ask for it in exchange that I don't reveal your secret to all of these people."

She couldn't help but giggle at Tyrel's offer. He was smiling, knowing how strange it sounded as well. She knew that he didn't have the info he was 'threatening' to use unless she gave him it, but she appreciated him going along with what she had asked for. In fact, she hadn't even know that this is how she would've wanted this to happen.

"You can stay living in your home, at least for as long as you want. Eventually you could always move in with me, but until then things would go like this: You always respond to my messages and you never say no to me. I want to see your apartment at some point, and if it's not right then I will tell you how I want you to re-do it. Understood?"

That was something she was happily surprised to hear, she hadn't even asked him to deal with her apartment, but the idea of being 'forced' to feminize her house was brilliant to her. She nodded and said, "Mhm."

"And also, at some point I want to introduce you to my wife. You will be both of our pet and you'll love it." He said.

She was shocked at that. She hadn't been aware that he had a wife, or that she was into this also. He hadn't mentioned it, and her obvious surprise seemed to give a bit of confidence to Tyrel. She said through her shock, "Oh... Okay."

"Perfect. So I then, are you game Kallie?"

"I... Guess so."

"Good. Then from now on you'll call me Master or Daddy, either works. Now, I want to dance, care to join me?" He stood up and held his hand out to her.

Her lasting surprise and strange look began to melt away into a smile as she stood up and took his hand. he led her through the tables and past the bar into the dance floor. The music was loud and she was beginning to lose her own thoughts to it. He backed up to the crowd and began to tap and shake to the rhythm, trying to coax her to do the same. She had never danced, but she began to just mimic his movements uncomfortably. He grabbed her hands and began to pull her into the crowd, fighting their way to the middle. The quick electric and quasi-rap music was booming through the speakers.