The Feminization Bet: The New Girl (TG-Empress)

InfectedRogue's 2nd commission for June 2024

Alan walked through the door of Roxanne’s apartment early in the morning after her very long night with Tim and Ben. Roxanne was asleep on the couch with her magic wand dangling from her hand. Alan chuckled a bit, she clearly had a fun night as well.

Alan then went to her bedroom and took a shower to clean herself. Once she was clean, she dried up and went back into Roxanne's room to rummage through her closet. Alan was going to dress herself up today and show Roxanne that this was something she really wanted and was now committed to.

So Alan picked out a cute white blouse, a thin bra with matching panties, a pink skirt, white thigh-high socks with black bands at the top, and finally a pair of black heels. Alan took them over to the bed and started to get dressed.

After that, it was over to the makeup table to put her wig back on and do her makeup. Once she was ready, she got up and walked into the living room and woke Roxanne up. She sat up and yawned then looked at Alan.

She asked her how her night was. Alan turned a bit red and said it was fun. Alan then asked how her night was, subtlety hinting at the magic wand in her hand. Roxanne looked at it and laughed, saying it was quite fun thanks to the sex pills.

Alan laughed, then asked why she needed them. Roxanne rubbed the back of her head awkwardly then confessed that she took it at the same time Alan did. Alan raised an eyebrow and asked what that meant.

Roxanne said that she put the pills into both wine glasses so Alan would get it no matter what. Alan was shocked, she had rigged the bet. Roxanne nodded saying it wasn't the first time either, she’d been doing it all week.

Alan was shocked. She asked about each bet, starting with the original. Apparently, the mallet was rigged to be heavier on one side, but she had practiced with it beforehand. Then she purposely made Alan walk around in heels to make her uncomfortable enough to take them off.

Which was the whole reason she was making this bet for the whole week. After that was the bet for the buttplug and chastity, which she rigged by swapping out the coins for a double-sided one without Alan noticing.

Alan already suspected she had rigged the bet at the beach with the guy, but she even rigged the bet at the strip club. How? Well, it turned out she knew the four guys they bet would grope Alan, and she asked them to do it.

The entire week had been rigged, making it so that no matter what happened Alan would end up feminine and submissive. Alan only really had one question, why did she do it? Roxanne smiled and said that she knew Alan very well.

She knew that Alan wanted to be a girl, and was very submissive, but repressed those feelings and desires in order to match what society told her she was. Roxanne knew the only way to get the real Alan out was to force her out and show her.

Alan was speechless, Roxanne was of course right. Alan would never have done any of this without her pushing her into the bets, and she never once refused to do any of it, because she loved it, she wanted it.

Roxanne apologized to Alan about it and asked her for forgiveness. Alan looked down, then out the window, and then said no. Roxanne was a bit surprised to hear that, and once again apologizing but said she understood.

Alan cut her off and said she didn’t finish. She said that Alan couldn't forgive her, because she wasn’t him, she was now Alana, and Alana could never be mad at her best friend, especially when she went to great lengths to help her be her true self.

Roxanne paused for a moment as she processed it, and then she jumped up and hugged Alana. She started by saying it was so amazing that she was choosing to stay like this, then saying they were going to do all kinds of fun things together.

Alana said that was nice, but they still had one more day left in the bet, and Alana wanted to know what she had planned for the day. Roxanne let go of Alana and smiled. She said that planned to get her to meet all her girlfriends.

She had hoped that Alana would decide to stay a girl by today and she could become a part of their friend group, but had she been wrong about her, and Alana was still going to turn back, Roxanne planned to humiliate her in front of the girls and expose her as a crossdresser.

Of course, they got the better outcome. Roxanne said she still might humiliate and try to embarrass Alana since she is very submissive and would probably enjoy public humiliation. Alana turned bright red and denied that accusation.

She then turned her head so that Roxanne couldn't see her smile as she thought about it. Roxanne then got up and went to her bedroom to shower and get dressed. Alana went over to the kitchen and started to make them breakfast while she waited.

Roxanne came out two minutes later and the two of them stood at the counter eating the food Alana made. After that, they went to the park to wait for Roxanne’s other friends to show up so they could begin their girl's day out.

Alana was sitting on a stone bench with her knees pressed together looking out into the park when the others arrived. Roxanne went up to talk to them first, then turned black towards Alana and told her to come over.

Alana got up smiling, brushed her skirt off, walked over, and introduced herself as Alana. The rest of the girls welcomed her with open arms and told her she was very cute. Then they suggested celebrating Alana and her coming out and joining the group they were going to take her shopping.

They brought her to the nearest clothing store and pushed her into a changing room. Then each of the girls went off to pick out items to make an outfit for her. Then Alana put them on and modeled them for all of them.

After which they would vote on if it looked good on her, and if it did, they’d get it for her. Alana ended up with five new outfits to go in her closet after she tossed away all the male clothes she no longer needed.

After that, they went over to the salon where they each got manicures and pedicures. They knew Alana didn’t have long hair yet so they were going to wait to get their hair done together, but they promised to do so as soon as she grew it out.

After that, they went out to lunch. They spent most of the time gossiping and talking about guys they’ve been with, which was when Roxanne mentioned Alana spent the last night with two really handsome ones.

That caused the rest of the group to ask for more details. So Alana spilled everything to them. Now they all knew she was a bit slutty and completely submissive. Now a group of guys would probably make fun of her hearing that, but none of the girls did that.

Instead, they gave her tips and suggestions on how to make it better for her next time, and that included some toy suggestions. Once they paid for lunch and started to pour out of the restaurant they were discussing where to go next.

That’s when one of them said the clubs were opening up soon, so they could go there, dance, and drink. One of the other girls then said they could do something even better than that, they could hit on guys and hook up, maybe even find some boyfriends.

Roxanne then poked Alana, asking her if that sounded fun. Alana turned bright red. She clearly had no problem sleeping with a man, but to actually date one? She wasn’t sure if she was ready for that, but she was off to find out whether or not she wanted to.

With that, the feminization bet was officially over. Alan spent the week as a girl and came out the other side as Alana. Now she’s off to meet some guys and hopefully find the one she’ll spend the rest of her life with, and it’s all thanks to Roxanne and the bet that completely changed her life for the better.