The Feminization Bet: Two Guys One Girl (TG-Empress)

InfectedRogue's 1st commission for June 2024
Uncensored version: https://www.patreon.com/posts/feminization-bet-106038960

Alan was in the middle of brushing his teeth, for the tenth time. He even rinsed his mouth out with Listerine, just to take the awful taste of feet out of his mouth. Once he finished, Roxanne came walking in withholding another dress. She handed it to Alan and told him to get dressed.

Alan looked at it, it was quite a bit smaller than the dresses he had been wearing up until now, plus there was nothing else with it, no socks, underwear, or even a bra. He looked up and asked her, but she said it was all a part of the plan.

She then left the room and started to get changed herself. Alan put the dress on over his shoulders, then pulled it down. He really had to pull it to get it to cover himself because it was so damn tight, but he did manage to get it on.

The dress was just a basic black dress, but it was the tightest one he’d worn so far. The waist was like wearing a corset and made him look slimmer. The chest was slightly padded, making it look like he had small breasts, and hid his nipples that would surely have been showing.

Between the pads, was a diamond-shaped boob window, which showed off the center of his chest, but that was it since he didn’t have any cleavage to show off, not that he was super any could fit into such a tight dress.

The dress ran down to his ankles in the back, but in the front, it barely went down to his thighs. Bending down, or a slight breeze would completely expose the thing dangling between his legs. Overall, it was a tight dress, but made him look and feel quite sexy.

He walked into the bedroom to find Roxanne in a similar dress, with open-toed heels and applying makeup. Alan noticed another set of heels sitting on the bed and figured they were his so he went and threw them on.

After that, Roxanne let him sit at her makeup table to do his own makeup while she explained the plans for the night. She had set up a double date with these two guys she’d been talking to. Alan knew there was something more, so he asked if this was one of those, back to his place dates.

Roxanne chuckled and said if that's what he wanted he could do that. Alan said of course he didn’t, but in his mind, he wasn’t sure, it didn’t sound that bad. Once he was done with his makeup, Roxanne and Alan started styling their hair.

Alan didn’t have to do much since he had short hair, so he’d been wearing a wig all week, Roxanne, on the other hand, had long super curly hair that she was trying to straighten. So after he got his wig on, he helped Roxanne do her hair.

Once they were both dressed they headed over to the restaurant to meet their dates for an early dinner together. When they arrived, Alan was introduced to Tim and Ben, their dates. Then all four of them went in and sat at a table.

They ordered drinks and a meal and had an amazing conversation as they waited for dinner to arrive. Right before dinner arrived, Tim and Ben went off to the bathroom and Roxanne leaned in next to Alan and asked him if he wanted to make a bet.

Alan said sure, then asked what she had in mind. Roxanne pulled two pills out of her purse and placed them into each of their drinks. They quickly dissolved and you couldn't even tell something had been put into it.

Alan asked what it was, and Roxanne said one was a sex pill and the other was a sugar pill. Roxanne had Alan close his eyes and she switched the drinks around. Then she told Alan to open her eyes and pick a glass and drink it.

If he got the drink with the pill, which would be very obvious in about a half hour, Alan would go home with both guys and let them fuck him, but if she got it, she would go home and let both of them fuck her.

Alan looked at her and asked if the guys were even into it. She smiled and said yes, they already knew about it, and about Alan, and they were in the bathroom taking similar sex pills so they could be ready when they got back and able to perform for hours.

Alan looked at the wine glasses, one glass meant a nice calm night of relaxation, and the other a long horny night of getting fucked. Alan reached for a glass and changed his choice several times before taking the one closest to him.

He put the glass up to his lips and Roxanne did the same, both of them then chugged the glass sealing this bet. The guys came back and looked at them and winked. Some time later their dinner arrived and they began to eat.

When they were close to finishing, Alan noticed something. His dress was starting to poke up. He slid his chair back a bit and looked down. His dick was starting to get erect. He gulped, it seemed he lost another bet, which meant he was going home with these guys.

Alan looked at Roxanne who looked down at his crotch and smiled. Roxanne handed him her purse to use to hide his erection and force it down so no one saw it as he left. Roxanne then excused herself and told the table to have a fun night.

The guys looked at Alan, smiled, and then called the waiter to get the check. One payment and a car ride later, Alan was standing in a bedroom watching two guys get naked. Once naked, Tim and Ben played rock paper scissors to see who gets to take his ass, and who gets his mouth first.

Tim one, and wanted to take his ass first with his nine-inch cock, meaning Ben was going to fuck her mouth with his ten cock. They asked him if he was ready and he nodded. He then got onto his hands and knees.

He pointed his head and butt upward for them. Both the guys grabbed some lube and started to stroke their cocks with it, then Tim came in from behind and grabbed her his with his hand and then positioned his cock at her back hole.

He then slowly inserted himself into him. Alan went to let out a moan, but it was quickly muffled by Ben’s cock slipping into her mouth. Alan was surprised to find it tasted pretty good. Ben noticed his surprise and said they picked a lube that could be eaten and taste like fruit.

He said something about it making it better for everyone, but Alan’s attention was quickly drawn to Tim began to thrust himself in and out of her butt. Seconds later Alan was barely managing not to choke on Ben’s cock sliding in and out of her throat.

The pills were really working their magic on all three of them. Both of them were super hard, and likely at their largest size by now, and that included Alan. His dick was a good two inches longer than it normally was, and it was throbbing like crazy and begging to be touched.

But both of them were too busy fucking him to help out with that, so it seemed not only was he going to have to them off, but he was going to have to get himself off. So he removed one of his hands from the floor and moved it down to his crotch and started to jerk off.

It didn’t take long before he cummed, getting it all over the floor and a bit of it on the inside of his dress. Following his lead, Tim filled his butt with cum, and Ben shot his down Alan’s throat. They pulled out and gave Alan a second to recover, and then they swapped spots and went again.

As they went for round two, Alan couldn't help but feel happy. He really liked this. He liked being submissive and getting fucked by handsome strong guys, and he really liked being a girl and didn’t want to stop now.

That was how Alan ended day six of the bet. There was only one day left. Alan had no idea what Roxanne was planning for it, but Alan knew he had to tell her about how he was feeling. There was only one more day in their bet, would Roxanne accept Alan as a girl even after it was over?