Melissa's Second Conquest

Melissa's Second Conquest by Michelle X

Hello, it's me again. Melissa, remember? I'm the one who makes a living out of turning men into women. A few weeks ago I told you about how I turned my jerk boyfriend Steve into a pretty secretary named Stephanie who now has a gorgeous husband. Well, I thought you all would be interested in hearing about my second conquest.

I had figured that my feminization of Steve would be my first and only one, but another challenge soon presented itself before me. About a few months after I dumped Steve, I got a call from a woman named Bev who had worked with Stephanie and had heard through the grapevine what had happened. Bev had tracked me down and called me with a proposition.

She was a single mother with a 16-year-old son named Trent. She told me that she was fed up with his obnoxious behavior. He was the typical asshole jock type, thinking he was the greatest and always screwing around with girls. "I'm just sick of him and his disrespect for other people, especially women," Bev told me. "I'm not liking the way he has turned out. I had always wished that he were born a girl, but I just figured there was nothing I could do about it. But now it seems like you might be able to help me out."

Bev asked me, quite simply, to turn her studly son into a beautiful girl. In return, she would pay me $5,000. At first I was reluctant, as I wasn't quite sure if I would be able to successfully perform another feminization. But the money was too good, the challenge too intriguing. I said yes.

Since Trent didn't know me, or vice versa, I knew it would be difficult to get him into a position where I could feminize him. But then I learned that the company I worked for offered a mentorship program for area high school students. Participating kids worked with employees over the summer to learn more about the business world. I knew this would be perfect.

So first I volunteered to be a mentor for the summer. I would be assigned about a dozen kids for the summer. Now all I had to do was have Bev get Trent to apply, and that would be it. I told Bev about my plan, and she told me that it sounded like a good idea and that she was sure she could get Trent to apply. Sure enough, an application from him arrived in just a couple of days.

I pulled some strings to ensure that Trent would be interviewed for my program. In a week, he came by, and sure enough, he was as big a jerk as his mother said he was. He was very cocky, acting as if he was overqualified for the job. I played along, telling him he essentially had one of the positions, and I tried to convince him to agree to participate.

"You're very lucky to be offered this position," I told him. "The other eleven positions have been filled by some very talented and intelligent girls."

"Eleven girls!" he said with a big smirk on his face. "It's going to be tough scoring with eleven girls in just three months. This will wear me out!"

"Actually," I said with even a bigger grin, "it looks like there will be one more girl joining us."

Trent agreed to the position. I had him sign a contract agreeing to participate in the program, which he quickly scanned and signed. He was now mine.

The first day of the program began the following Monday. Everyone was supposed to meet in my office at 9:00 sharp. The eleven other girls had arrived on time, dressed in sharp suits. Trent had arrived late. Trent waltzed in at 9:30, dressed in khakis and a shirt and tie.

I looked at him and said, "Excuse me young man, what exactly do you think you're wearing?"

He looked at me with a puzzled expression. "What do you mean?"

"Did you not read about the appropriate dress code when you signed your contract?"

"Yeah, I guess. What's wrong?"

I pulled out his signed contract and read: Section 4: One of the goals of this program is to learn about appropriate business attire. Thus, all participants will agree to wear the following every day: a dress, or a suit with an appropriate blouse and skirt; nylons and heels between 2-4 inches; jewelry and makeup as appropriate.

"I don't see you wearing any of those things," I snapped. "Didn't you read the contract?"

"I think I saw that," he said in a cocky tone. "But that obviously didn't apply to me. I just figured you put that in because you didn't expect to have a guy working here. I so wore the equivalent guy's clothing."

I shook my head. "Trent, one of the first things you have to learn about business is to always know what's in a contract before you sign it. This is a legal document, and you are bound to it. I'm not making any exceptions for you. All the other participants are wearing the proper clothing, and you will do the same."

"No way, bitch!" he yelled. "There's no way I'm dressing up like some little fairy! My mom's a lawyer. I'm going to call her up and tell her to settle this once and for all."

I told him to go ahead. He followed through on his threat, and came back with a grin saying, "She's coming right over.

Bev arrived half an hour later, acting confused but knowing exactly what was going on. I repeated what I had told Trent. "I see," she said. "Well, there's no problem here. This is something that can be easily fixed." Trent nodded with approval.

"Trent," she said, we're just going to have to get you some new clothes." You should have seen the kid's jaw drop!

He started whining and whining, but his mother would not relent. She even got vicious. "Listen, you brat, stop embarrassing me! You agreed to be a part of this program, and you can't back out of it now! You made me look like an idiot, rushing over to defend you when you didn't read the stupid contract!"

Bev turned to me and said, "I'm sorry for this misunderstanding, Melissa. I'm going to take him out, and in a few hours he will look more appropriate."

So she took her distraught son away. I could hardly contain my joy. I knew that the new few hours would be the last he would ever spend in male clothing for the rest of his life.

Later in the day at about 2:00, I was giving the other girls a tour of the building, when I heard a pair of high heels clicking their way toward us. I looked up, and saw what appeared to be a very unhappy teenage girl. She was dressed in a navy blue suit with matching hose and heels with a white blouse. She had what appeared to be a recently done perm, colored to a golden blonde. She had the most exquisite makeover, with full, cherry- covered lips, long, thick eyelashes, and long fingernails painted to match her lipstick. She wore a pair of dangling earrings and reeked of perfume. There was no doubt who it was.

"Hello," he said meekly.

"Well, I'm glad you changed your attitude so quickly," I said. "You look very pretty, Trent. Actually, it would be pretty stupid for me to call you Trent, wouldn't it? You need a new name. How about Tracy? Yes, that sounds good. When you get your ID badges, we'll have to remember to put that on yours."

I turned to the rest of the group. "From now on girls, you must call her Tracy, not Trent. And please don't be cruel. I'm sure Tracy is embarrassed enough as it is. Don't think of her as a guy, though I don't know how you could when he's wearing such a feminine outfit. Just treat her like one of the girls. After all, that's what she's going to be for the next three months."

Trent looked completely defeated. No longer was he arrogant and cocky. He had been put in his place, and now he was demure and polite.

The rest of the day went pretty uneventful, and at 5:00 Bev came to pick Trent up. It was clear that he was looking for some support, but he sure wasn't going to get any from his mother.

"Well, did you learn something today?" she said in a snippy tone. "After all your cockiness, I'm kind of glad to see that you have been knocked down a peg. I think this will be a good thing for you. You always thought guys are great and that women are just supposed to please the guys. Now the shoe is on the other foot. Or should I say the high heeled shoe?"

And they left. Later that day, Bev called me to tell me all that had happened. She said that they first went to the mall, where first picked out about a dozen or so outfits, mostly conservative suits in professional colors. They also picked out appropriate bras, pantyhose, and heels to go with the outfits.

"But he just thought it was a game," she told me. "He seemed less than enthused about trying on the clothes, acting like he never would really be wearing them. Boy, he has no idea how long he'll be wearing them!"

"Anyway," she continued, "he first he got scared was when I took him to the beauty salon. You could just see the terrified look to his face when he realized that we were making permanent changes to his hair, eyebrows, and finger nails. You could tell that he wanted to escape, but of course there was nothing he could do. He just had to sit there and accept his feminization."

I asked Bev how he was doing now. "Not too good," she replied. "He's still wearing his skirt, blouse, hose and heels right now. I told him that he needed practice in being a girl, so I told him that he had to wear his work clothes all through the day. None of his male clothes are allowed. And in fact, tomorrow while he's with you, I'm going to pack up all his old clothes and send them off to Goodwill. Just in case."

I was thrilled. My plan was going perfectly, and Bev wanted to be an active participant in the feminization of her son. It would be the easiest and most enjoyable $5,000 I had ever made.

Tomorrow, Tracy was definitely not late. She arrived promptly at 8:15, dressed in a brown suit with a cream-colored blouse, with brown pantyhose and shoes. Again the makeup and hair were perfect.

After that first day, things went fairly normal. Resigned to his fate, Trent began acting like any other teenage girl. The other girls refused to acknowledge in any way that he was ever a guy, which seemed to make him angry. At lunch, he would try to talk with them about guy stuff like sports and cars, but they just ignored him and began talking about clothes, makeup, or cute guys. At first, Trent refused to join in the conversation, but it appeared that he was getting lonely, so he began joining in. I must say, it was very amusing when I first heard Trent talking to the girls about a makeup tip he had read in Mademoiselle.

Every so often, Bev would get in touch with me to let me know about the progress of Trent's feminization. "Oh, Tracy threw a big hissy fit when I told her that I had gotten rid of her male clothes. She kept on whining about walking in heels all day and being on display for all the men. I had no sympathy for her."

"Last week I started getting even tougher. I took away all his posters of bikini-clad women and all his Playboy magazines. Instead I gave him some posters of Ricky Martin, Mark-Paul Gosselar, and some other hunky men, which I forced him to put in his room. And in exchange for his Playboys, I gave him a box full of my Playgirls. I don't think he's touched them yet, but I'm sure he'll turn to them someday."

"And now I'm going even further in erasing his identity as Trent. There used to be a bunch of photos of Trent hanging all around the house, and I've replaced them with photos of Tracy that we took at Glamour Shots. And now I've refused to call him Trent anymore. I just call for Tracy. At first, he wouldn't reply when I called him Tracy, but I think he's coming to realize that I'm never going to call him Trent again."

I didn't want Bev to have all the fun in Trent's feminization, so I decided to add a further twist. One Friday afternoon, I called all the girls into the office and told them I had a big surprise.

"As you know," I said, "there are other student participants in the mentorship program working in other offices. I think it would be nice if you could meet with them. So I've arranged for a dinner tonight at a fancy restaurant, and I've found some nice students who will be your dates. Get ready to go, because we leave in fifteen minutes."

Trent raised his hand and said, "Excuse me, how I am going to go out on a date with another girl when I'm dressed like this?"

"What makes you think you're going out with a girl?" I asked.

He looked positively frightened. "A guy? You want me to go out with a guy? No way. I've been a prissy queen for you this summer, but I'm not acting like some queer!"

I let out an exasperated sigh, and said, "Tracy, this is really getting tiresome! Why do you keep expecting that exceptions will be made for you? You are going on a date with a boy tonight, and that's final! He's actually a nice boy. His name is Jason McNulty, and he's very good looking and popular."

The other girls looked positively jealous. They all seemed to know how much of a hunk Jason was, and they told Tracy that she was so lucky to have him as a date. They all told him about how big and muscled he was from being captain of a football team.

In a few minutes the guys walked in, looking handsome and dressed in their sharp suits. All the girls turned their heads to one young man in particular, tall with blond hair and blue eyes and an extremely muscular frame. Everyone except Tracy was swooning over him.

"Jason," I said to him, "this is your date Tracy. She's a little bit shy around guys, but I'm sure you can turn her around by the time this night is over."

Jason looked at his date with a huge smile. "Tracy, you're gorgeous. I think we're going to have a great time tonight."

I gave everyone directions to the restaurant. Jason drove Trent to the restaurant, so I didn't see them again until they got there. They had arrived a little late. He said he was stuck in traffic, but who knows what really happened? They looked so cute when they walked into the restaurant. They were holding hands like a couple who had been in love for years. Trent looked so helplessly feminine. Even in his heels, Jason still towered over him. I could tell that he kept trying to pull his hand out of Jason's, but he was powerless.

When the entire group had assembled, I made an announcement. "Well, it looks like I goofed when I made the reservations. We have two more people than our reserved table can hold. That means that one of the couples will have to eat by themselves on the other side of the restaurant."

As expected, Jason instantly volunteered. Trent looked positively shocked. He was at least expecting to have safety in numbers for the night. Now he would have to fend for himself with Jason all alone. With a scared look on his face, Trent was dragged away by Jason to their cozy table.

Throughout the evening I would periodically take a look across the room to see how the lovebirds were doing. Jason had seemed like such a charmer. Trent, obviously sickened and humiliated by the situation, refused all of his advances, and I correctly predicted that this would stir on Jason all the more. Indeed the entire evening, whenever they weren't eating, Jason would stroke Tracy's hand, put his arm around her, or giver her playful kisses on the neck.

After they had finished eating, Jason dragged his date onto the dance floor for a few slow dances. I'm sure Trent tried to do whatever he could to pull out of his date's arms, but he was no match for Jason's masculine power.

Later in the evening, Jason took Trent out into the courtyard, when all of a sudden I saw Bev, who had come over to do a little spying. I related to her what had happened, and she was beaming. She asked me where Tracy was now, and I took her over to the courtyard, where we got quite an eyeful. Jason and Trent were sitting on a bench, necking passionately. Jason had his strong arms wrapped around his date, and Trent had to sit there helplessly while this football stud was putting the moves on him.

We watched for about 10 minutes, and it became clear that Jason wasn't going to stop any time in the near future. I asked if we should interrupt them, but Bev just said to let them be and have their fun. I just assumed that Jason would drive his date home, so Bev and I left.

The next day Bev told me that around midnight, she heard Jason and Tracy enter the home, and they continued to make out for about another hour. After Jason left, she heard Tracy cry herself to sleep.

Trent's ordeal got even worse the following Monday. I kind of let it slip out to the girls how intimate he was with Jason the other evening, and as soon as Tracy arrived at work, they all giggled and asked how the date was.

"Tracy, isn't Jason such a great kisser! Did he French kiss you?"

"Tracy, what's that on your neck? Is that a hickey?"

"Tracy, I'll bet you've been dreaming about his broad shoulders and rippling abs all weekend!"

Trent just blushed and ignored them. But the humiliation wasn't over yet. During lunch, Jason came in to surprise Tracy, carrying a bouquet of roses. The other girls giggled. In front of everyone else, he told Tracy how pretty she was, what a good time he had, and that he wanted to go out on another date. "And I won't take no for an answer," he said.

Trent tried to resist, but Jason persisted. "I'm not listening, Tracy," he said. "I said I won't take no for an answer. I'll pick you up after work on Friday."

Trent looked so helpless. Little did he know that what he thought would be a one-time date would soon be developing into an ongoing courtship.

Not too much else happened until a week later, after Jason and Tracy had gone on their second date. Jason again decided to drop by during lunch. "Gosh, I said, "you're coming to visit Tracy so often, I'm beginning to think that you guys are boyfriend and girlfriend."

"Oh, we are!" said Jason with a big smile, as he sat down next to Tracy and put his arm around her. "I told Tracy that I wanted us to be a steady couple. She didn't say no, so I guess she's now my gal."

Trent just squirmed in his seat, knowing that there was nothing else he could do to get out of his embarrassment. As Jason got up to leave, he said, "Where's my good-bye kiss?" He pulled Tracy up and toward him, wrapped his arm around her and gave her the biggest kiss. Tracy was powerless to do anything but give herself to her boyfriend. I'm sure Trent was just utterly humiliated by having to kiss the guy in front of everyone else.

Jason's lunchtime visits soon became a daily habit. Trent was obviously uncomfortable, but he soon learned to play the role of the submissive girlfriend. He seemed much more willing to be physical with Jason. After all, Tracy was in no position to give orders to this tall, strong young man who could easily overpower her.

I hadn't heard from Bev in a while, so I decided to give her a call and see how things were going on her end. "Oh," she said, "I'm having so much fun thinking of new ways to erase my son's old identity and force a feminine identity upon him."

"For example, now that Tracy has started dating Jason, I've told her that she needs to get a more girlish figure. So I signed her up for aerobics classes at the women's gym. I bought her some nice pink spandex shorts and sports bras to wear to class."

"I was worried that she might look too masculine, but believe me, she doesn't resemble a guy in any way now. All of her muscles have atrophied, and her waist has dropped at least 8 inches since she started working for you."

"Also," Bev continued, "most of her other features have become undeniably feminine. Her fingernails have grown to the point where she doesn't have to wear press-on nails anymore. I think she's still taking a while to get used to those. She's learned that with her long nails, her movements have to be more delicate and graceful. I swear, Tracy looks so frustrated trying to maneuver like a male, but trapped by her own features, she can't help but act feminine, no matter how hard she tries not to. I actually think her feminine mannerisms are becoming ingrained in her. I bet even if we let him dress like a boy again, he'd never gain his masculine mannerisms back."

"And her hair is becoming more lovely as well. It's becoming long enough that we can give her more feminine cuts. I make her go to the beauty salon every two weeks to fix it up. When she goes, she also gets a makeover and a manicure."

"Yet I still can't get how stupid he is!" Bev exclaimed. "With all this, he still thinks that I'm going to let him go back to being a male. For instance, he told me that since he would be starting school next month, I should get him some 'normal' clothes! If only he knew that the skirts, blouses, heels, and pantyhose he's wearing for the summer ARE now his normal clothes, and will be that way for the rest of his life!"

I was pleased to hear that everything was going great with Bev. I knew that Trent had absolutely no hope. Not even a miracle would ever get him out of skirts for life.

As the summer was winding down, I'm sure that Trent started getting more and more nervous. The new school year was quickly approaching, and Bev had not mentioned any plans whatsoever about his return to being a guy. I could tell he was longing for a pair of loose boxers instead of his tight sheer pantyhose. I'm sure he would do anything to get out of his pumps and into sneakers. But that was never meant to happen.

So the final day of the summer program was approaching, and I knew that was time for me to put the final nail in the coffin. I decided to set up a little "awards ceremony" for the last day, and invited the girls' mothers to attend.

All the mothers showed up beaming with pride, including Bev. I'm sure Trent was expecting that as soon as it was over, he could tear off his blouse and skirt and go back to being a guy. In reality his life as a woman was just beginning.

I concluded the ceremony, saying, "And our last award will be a very special one. It can only go to the one girl who put forth the most effort throughout the summer. For recognition of such hard work, we will offer her the opportunity to have an after-school job here during the year. In addition, the award winner will receive a college scholarship!"

"Our winner was a very special girl. She was subjected to some unusual ordeals throughout the summer, but she made it through with flying colors while being a good sport. So, without further ado, our big award winner is Tracy."

Bev hugged Tracy, who shook her head with a look undoubtedly suggesting, "No, I don't want it!" But I just shoved the award certificate in her hand and gave her a hug. "I'll be looking forward to working with you throughout the year," I said.

All the other mothers, and girls left, so then it was just the three of us. Trent turned to me and said, "Thank you for recognizing me, Melissa, but I can't accept this award. I know you're going to make me dress as a girl if I accept it. I'm sick of doing this! I'm NOT a girl, I'm NOT a pansy, I'm NOT a fairy! I refuse to do this any more!"

Immediately Bev slapped his face. "Listen to me young lady! Melissa was generous enough to offer you a job and scholarship money, and you're going to disrespect her by refusing it? Absolutely not! You're not going to pass up this opportunity because you don't like your clothes! I think you should get this ridiculous idea out of your head that I'm ever going to let you dress as a boy again!"

"No, no, no!" he yelled.

"You don't have any choice, missy!" Bev said. "I have only one child, and her name is Tracy. In my mind Trent does not exist, and he has never existed! If you don't accept this, you're just going to have to leave home and fend for yourself! Although I'm not quite sure if you'd like living on the streets dressed as you are!"

At this point, Trent knew that he was beaten. This summer escapade would now be a lifetime of skirts, hose, and heels. Instead of working on his broad shoulder muscles and his bulging pecs, he would now have to spend all his time doing his nails and hair and dieting to maintain a feminine figure. Never again would be the big stud on campus with the hot girlfriend. Now HE would be the girlfriend, forced to submit to a boyfriend of his own. No longer could he drool over the hot women in the short skirts. Now that he was wearing the skirt, he would know that every minute of every day he would be leered at by the big, sex-hungry men who would dream of manhandling him.

So more changes started happening for Trent. Bev bought him more heels, skirts, and blouses for school. She had taken him out of his original high school and transferred him to the same school as Jason so that they could spend more time together.

And every day after school, Trent would work for me for two hours every day. He had appeared to become resigned to his inevitable fate, and soon he was behaving like any typical working girl.

As the year passed by, I kept on forgetting that Trent was ever a boy. I couldn't even remember what he looked like as a guy. I'm sure he had forgotten his old identity as well.

One day in winter, Trent asked me if I would write a college recommendation for him. I guess this meant that he would be applying to college as a girl, which meant that after college he would have to apply to a job as a girl. Yes, his fate was sealed.

"Oh," he said, "can I leave early today? Jason's taking me out for dinner and dancing. It's our six-month anniversary."

"Absolutely," I said. "You two are such lovebirds. I hate to be intrusive, but I should ask. Does Jason, um, 'know' about you?"

"Yes", he said reluctantly. "All the other girls blabbed about it to him. But he doesn't mind. Right now in my life, he's the only good thing I have. I still think it's disgusting being physical with him, but what can I do? After all, I'm the girl and he's the guy, so he gets to call all the shots."

"Besides, he's so much stronger than me, so it's not as if I can stop him when he wants to get more intimate than I want to be. But I've learned to give in to him. I don't want to lose him, so I'm willing to do whatever he wants."

In a few minutes, Jason walked in, coming to get his girlfriend. As the happy couple left, I reflected on how much Trent he had changed. Once a cocky male, he had now learned to accept his role as a submissive female. As a guy, he wanted girls to satisfy his raging physical urges, but now he would spend the rest of his life fulfilling other men's physical needs. He was beginning to understand womanhood, and like it or not, that was his fate.

My work was done.