Riley Gendreau
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The feminization bet (TG-Empress)
🕑 Added 2023-12-29 16:54:39 +0000 UTCInfectedRogue's monthly reward December 2023
Alan and Roxanne were best friends, but they were also super competitive with each other. So much so that they always tend to bet on whatever activity they're doing. Most of the time the winner will get something petty like praise from the loser or make the loser do something embarrassing.
As it was all in good fun, neither one backed out and would always fulfill their end of the bet if they lost. That was until Alan made a bet that he was certain was impossible to lose. While at the arcade he bet Roxanne that he could get a higher score on the strength test.
She laughed at him. It was a bit of an unfair challenge since he was stronger than her, but she agreed to it, but instead they up the reward. Alan was so sure of himself that he actually agreed to let Roxanne completely feminize him if he lost.
In exchange, if he won she would give him a lap dance wearing nothing but a skimpy bikini. With a handshake, the bet was officially on. Alan let Roxanne go first that way he could know how hard he had to slam the mallet to win.
Roxanne went and to Alan’s surprise when she slammed the mallet down the ball went nearly to the top. So he had to hit it as hard as possible to not risk losing. He picked up the mallet and looked down at the spot to hit.
He just had to make the bell ring at the top and he’d win. He lifted the mallet up and swung down as hard as he could, but his aim was a little off and he only hit the side of the pressure plate that activates the machine causing it to only go halfway up.
His jaw dropped as Roxanne began to giggle. Alan tried to negotiate for another chance double or nothing but Roxanne wasn’t interested in that. She grabbed his hand and led him to her car ending their arcade trip early.
She drove them to her house and pulled him inside her room where she already had a ton of beauty products, clothes, and even a wig waiting. Alan was a bit confused and asked if she expected this to happen. To which she just nodded and told him to get undressed.
He sulked and started to remove his clothes until he was down to his underwear. He then watched as Roxanne started to pick up sexy dress after sexy dress. That’s when Alan begged her to go easy on him, maybe just make him look tomboyish instead of completely feminine.
She laughed and told him no way. She said he possibly wouldn’t let her do this again, so she was taking full advantage of it. She then tossed him padded panties. They would cover his dick and make his butt and hips look wider.
He slipped his underwear off and slipped them up, as soon as they were up Roxanne threw a pair of panties at him to cover them up. Alan then slipped them up, now bright red from embarrassment. Roxanne then walked up to him.
She was holding a small pair of breast forms, ones that have an adhesive side. She stuck them right to Alan’s chest. They dried within a few seconds and were now very stuck. He was fiddling with them as Roxanne walked back to her bed to grab a dress.
When she turned back around to face Alan, she had this very tight pink dress in her hands. It was definitely something Alan never imagined he’d wear. She turned him around and helped put the dress over his head and slip it down his body.
From there she sipped the back up and got the back of the choker around the button that holds it in place. She then had Alan turn around for her. Then she asked Alan how he felt in the dress. Alan still bright red remained silent.
The dress was tight, and it was a bit hard to move around in, but he had to admit with the addition of the breast forms and padded panties it did look like he had the body of a woman. Roxanne took his silence as him liking it and had him sit down on her chair while she went to the bathroom.
When she came back she had a razor and shaving cream. When Alan asked what she planned to do with that she gave him a look that easily read as, you know exactly what I’m going to do with this stuff.
He wanted to protest, but that would basically be backing out of the bet, and he still wasn’t willing to do that, especially if he wanted her to continue making bets with him so he could get his revenge for all this. The thought of revenge put his mind at ease.
Somehow it was enough o not let this bother him anymore and he happily let her do what she wanted all while thinking of ways to get back at her. Roxanne having no idea why his mood suddenly changed went away at removing hair from all the areas the dress didn't cover.
Legs, arms, chest, and face, no spec of hair remained on them when she was done. She tossed the shaving supplies to the side grabbed a pair of very high heels and put them on Alan’s feet, leaving him very confused.
His feet were definitely bigger than hers, so why did she have them in his size? How long was she planning this? Before he could get another thought in Roxanne turned the chair very quickly making Alan face the mirror.
Roxanne stood behind him and started messing with his hair. She seemed annoyed that it was short, so she put a bald cap on his head, pulled out a blonde wig, and secured it to his head. She tugged on the sides to make sure it wouldn't come off and then walked around to his front.
Alan had no idea what was what, but Roxanne was grabbing makeup and applying it to his face. Bit by bit Alan watched as his face changed from a male-looking one to a female one that he didn’t even recognize.
She finished by giving him fake eyelashes. Alan had reached up and was about to touch his face when Roxanne grabbed his hand and told him not to do that as it would ruin the makeup. Then she looked at his fingernails.
She scolded him for the horrible condition they were in. She said just because he was a man didn’t mean he needed to have nasty fingernails. She then trimmed them down and filed them before she glued on a set of fake longer nails.
Once the glue dried she started to paint them, and of course, she had to use a pink that resembled the bright pink dress Alan was wearing. She then demanded Alan place his hands flat in front of him while his nails dry.
Alan sat there hands flat on the table as Roxanne continued to so more things to him. It started with her testing out different accessories until she settled on putting bows in the wig he was wearing since they matched the dress.
Then finally she grabbed her perfume and sprayed Alan a few times. Roxanne told Alan to admire himself in the mirror while she cleaned up and put everything away while reminding him his nails were still wet.
Alan looked in the mirror. It was really hard to believe it was him under all that makeup, dress, and wig, but it was. It was almost impressive how those things can make a person look drastically different, or maybe it was just how good Roxanne was.
One thing was for sure, there was no way anyone was going to think the cute blonde girl was Alan. Ten minutes pass and Roxanne finally finishes sorting her stuff and putting them away. She walks over to Alan and inspects his nails. She tells him they should be dry enough now.
She then turns his chair and grabs his hand helping him to his feet since he’s not only in heels for the first time, but very high heels. She helped him walk back and forth a few times until he figured out how to keep his balance.
A few minutes after that his feet started to hurt a bit so he sat down on Roxanne’s bed and lifted his leg up to adjust the heel a bit, not that it would help much. Roxanne then made a joke about how cute he was.
Alan figured she was messing with him so he smiled and was about to make a joke back at her when he heard the sound of a camera taking a picture. He looked up and his eyes got wide as he saw Roxanne holding her phone with it pointed at him.
He stood up and wobbled a bit, then asked her what she was doing. She shrugged her shoulders saying she never wanted to forget this moment. Alan tried to get over to her and grab her phone to delete the pictures, but Roxanne was barefoot and able to move around quickly.
Roxanne asked what the big deal was, no one was going to know who he was, not dressed like this at least. Roxanne just wanted to be able to remind him about this day forever. He sighed and asked if she was done.
She said yes, but said he wasn’t allowed to change yet, and he had to spend the rest of the day dressed like this. He tried to protest saying it wasn’t part of the deal, then she asked if he was willing to make another bet.
He smiled and said hell yes. So the two made another bet. Alan would wear the outfit he was in now for the rest of the day, and if he removed a single piece Roxanne would win and he’d have to stay feminized for the whole week.
If Alan won, not only would Roxanne have to wear that skimpy bikini for a week, but she’d have to do everything Alan asked her to do. It would have been an easy bet if they had remained inside, but Roxanne dragged him out for a night on the town.
As anyone but Alan could imagine walking around for hours in tall uncomfortable heels is very harsh on the feet, and the second she removed one for a split second to get some release Roxanne caught him and he lost the bet. He had a long embarrassing week ahead of him.
Comments
last_of_workers
Quite an interesting plot, plus they have a very interesting relationship, and although cross-dressing is not exactly what I prefer to see, this particular story looks pretty good, overall I liked it
