The feminization bet: Shopping Spree (Early Access) (TG-Empress) (Patreon)

InfectedRogue's 1st commission for April 2024

Alan woke up on Roxanne’s couch. His feet were killing him from wearing those heels all day yesterday, and even worse he was still wearing the sexy pink dress Roxanne forced into as part of their bet.

Alan sighed and figured he would get out of it, but then his face grew bright red as he remembered he had lost the bet and would have to spend the entire week crossdressing. He held his face in embarrassment as Roxanne left her room to check on him.

She said she was glad he was awake. She had to get Alan dressed up for the day, as they had a lot of stuff to do. Alan asked her if there was any way he could get out of this, and she said sure, but only if he was willing to make another bet.

Alan frowned, with his luck so far it was best he didn’t do that before a week turned into a month. So he sighed, buried his pride, and made his way to Roxanne’s bedroom where he had his makeup and hair redone.

Roxanne helped him out of the dress he was wearing but got him right into another. It was still bright pink, way too short for his liking, and was padded so it looked like he had small breasts. After that, he was once again put into another set of heels.

Now that he was ready, Roxanne pushed him out of the way and started to get ready. While she was doing that, Alan asked what she had in store for him that day. Roxanne didn’t respond right away, as the thought of it was apparently so amusing she couldn't stop giggling.

Once she did respond, she told Alan he was going shopping. Alan thought that was a little strange, why get this dressed up to go buy food? Not thinking about it much, he sat down on Roxanne’s bed and patiently waited for her to finish.

Once she was dressed, the two went to her car and headed into town to their first stop. They walked inside and Alan quickly realized it was a makeup store, filled to the brim with everything a girl would need, from makeup and hair products to devices like hair irons and hair dryers.

Roxanne grabbed one of the shopping baskets and handed it to Alan, then told him to follow her around while she picked stuff out. Roxanne grabbed a ton of stuff. Mascara, eyeshadow, foundation, hair ties, hair brush, fake eyelashes, seven nail polish colors and fake nails.

There was easily a hundred dollars worth of stuff in the basket. Roxanne checked the basket to make sure it was good, handed Alan her credit card, told him to go pay for all this stuff, and said he wasn’t allowed to use the self-checkout aisle.

Alan turned bright red and begged her not to make him go buy all this makeup in front of a real person. Roxanne smiled and waved him goodbye as she left the store, telling him he wasn’t allowed back into the car with her stuff.

Not wanting to walk home in this dress and in these heels, Alan went over to the checkout and started unloading the makeup. The woman at the register looked at Alan and all the stuff strangely for a minute then smiled.

She said Alan had really good taste, which made sense as she looked super cute. Alan was a bit relieved she didn’t notice he was a guy or at the very least didn’t say anything about it, but also he felt quite warm inside from her complement.

Alan then paid for all the stuff and waved the woman goodbye as she left the store more cheerful than when she arrived. Roxanne noticed this and didn’t say anything, instead, she thanked Alan and asked him if he was ready for the next store.

Alan nodded saying he just wanted to get this over with. So they went to the next store. This time it was a shoe shop, well more specifically a shoe shop that specializes in making heels. Roxanne and Alan walked inside and Roxanne went right to an attendant and asked for help.

She told the woman that Alan needed her feet measured and wanted to try on a ton of heels. The woman seemed happy to help and had Alan sit down. She removed the heels he was wearing and put a nylon sock over his foot.

Then she took one of those foot-shaped measuring things, put his foot into it, and got his exact size. She then asked what types of heels he was interested in trying out. But before he could say anything Roxanne chimed in giving out a whole list.

She wanted him to try a pair of open-toe, wedges, thigh-high boots, knee-high heels, a pair of Mary Janes, and finally several things that had heels at least seven inches tall. She didn’t care what type they were.

The woman wrote it all down and went into the back, coming back with a literal cart of heels. Then one by one she’d help Alan into them and secure them on his feet. Unfortunately for him, just looking at them on his feet wasn’t good enough for Roxanne or the worker.

So they made him walk around back and forth in them, and they even pressured him into stunting around like a supermodel. After an hour and nearly falling over in the seven-inch heels, the worker asked which ones Alan liked.

Roxanne said them all and asked the woman to ring them all up. Alan was a bit surprised as it was nearly five hundred dollars, and for what a joke? It wasn’t like he was going to wear them again after the end of the week right?

In the end, it was her money and Alan concluded she’d just wear them herself after the bet was over. She had Alan once again use her card and they two carried the boxes of heels out to her car and loaded them up.

Roxanne said they had one more stop, but as it was now lunchtime, she was stopping by a fast food place to pick something up. Alan liked that idea as it would be the easiest thing they did today as he wouldn't have to do anything.

Boy was he wrong about that. Roxanne gave him a list of what she wanted and then said he could get whatever he wanted, but he had to go in and order. Alan asked why they couldn’t use the drive through and Roxanne once again smiled and ignored him.

So Alan walked in, stood in line, and waited to order. The whole time he could feel the guys around him looking at him, and he even heard a few of them talking about him, and suffice to say they all thought he looked sexy.

When he went up to order the guy working the register went from looking moody to seeming quite cheerful. He took Alan’s order and told him it would be out right away and had to stand at the front of the line to pick up stuff, despite other people already waiting.

It took about two and a half minutes but Alan got his order, thanked the guy, and went back to the car to eat with Roxanne, where he learned the guy had slipped his number into the bag. Alan was incredibly humiliated by it, and Roxanne was completely amused.

After eating they made their way to their last stop of the day, a lingerie shop. Alan was frowning and bright red again as he realized what was about to happen, but he didn’t bother complaining about it or trying to get out of it, instead he just followed Roxanne into the store.

They went to a changing room, and Roxanne had Alan get undressed, then used the measuring tap to find out his bra size. Then she said she was going to go find him a couple of sets to try on. Alan was too embarrassed and said he couldn't take it anymore.

So he said he was willing to make another bet. If he wins, he gets out of this and doesn’t have to spend the week crossdressing. Roxanne said to take that bet he’d have to risk quite a lot, and he said whatever she wanted he’d agree to it.

Roxanne smiled and opened her purse. She pulled out a small butt plug and a chastity cage. She said she’d agreed to the bet only if he was willing to wear this until the end of the week. Alan gulped but he wanted out so he agreed.

Roxanne asked what he wanted to bet on. Alan wanting to get this over wanted something that would be resolved instantly. So he said a coin flip. He picked tails, which gave Roxanne heads. Alan handed her a coin and told her to flip it to be fair.

She flipped it letting it land on the floor of the changing room so they could both see it as it landed. When it did, the head side of the coin was showing, meaning Alan had just lost again, and the head of that butt plug was going up the tail end of his ass.

Roxanne left Alan with the chastity cage and buttplug figuring he could get them on alone and she went to go find some cute bra and panties sets to put him into, and perhaps a few sexier things as well.

Alan stood in the changing room bright red. He knew there was no way out of it. He started with the chastity cage, he slipped it over his dick and secured the locking part around his balls, then he took an actual lock and clicked it into place, trapping his dick in the tiny cage.

Even worse than that, the outside of the cage was flat so instead of looking like he had a male chastity cage on, it looked more like he was a woman. At least it wasn’t as bad as the other thing. Alan had never had his ass penetrated so he had no idea how this was going to feel.

He bent over and started to push it in, and at first, it hurt a bit, but as soon as it was inside it felt sort of good. He actually somewhat liked it, but that turned out to be a problem. His dick started to try and get erect.

He knew right away this was going to make the rest of the week unbearable. Roxanne reunited holding nearly three dozen bra and panties sets, looked at Alan’s cage, and smiled. She then handed him the first pair to try on. It was a long embarrassing second day, and he still had the rest of the week ahead of him.