The feminization bet: Beach Trip (TG-Empress)

InfectedRogue's 2nd commission for April 2024

Alan woke up in his bed with Roxanne asleep next to him. It was strange that she was over at his place, but she insisted he take everything they brought back to his place. While she was asleep, he went to the bathroom.

He removed his butt plug, cleaned it off and went to the bathroom then took a shower. When he got out he saw Roxanne messing around in his bedroom pulling something out of the bag. So he reluctantly inserted his butt plug, grabbed a towel, and went to see what she was doing.

Roxanne was pulling out a couple of sets of bikinis with some beach wedges that she had bought yesterday. She held up a frilly pink bikini towards Alan and said he would look perfect at the beach in it, then tossed it to him.

He asked if he really had to wear this, and Roxanne said yes unless he wanted to make another bet. Alan quickly nodded and started to put it on. He got it on, and she tossed him the shoes, which easily slipped on and weren't as uncomfortable as the heels he’d been wearing.

Roxanne then changed and went off to Alan’s kitchen to pack stuff for their trip to the beach. Alan stopped her and asked if there was anything he could wear in the meantime, as he didn’t want to walk around all day in a bikini especially if they weren't at the beach.

Roxanne nodded and told him to deal with it, and then went to the kitchen. She made several sandwiches and packed a ton of water and soda into a collier Alan had then loaded it up into her car. Then she went back to Alan in his room and dragged him out of the house.

The whole time he was covering his crotch embarrassed, which made it easier for Roxanne to push him around. After a few minutes she got him in her car and the two were off to the beach for the day. It took about an hour but they arrived, and Roxanne kicked Alan out of her car.

She then grabbed the cooler and a beach umbrella she had in her car. She then locked the car so Alan couldn't hide in it. After that, they walked down the beach to just above the water and set up. Roxanne laid out two towels for them to lie on, followed by setting up the beach umbrella.

The two lay there and chatted as they drank some water. That’s when Roxanne noticed some hot guys Nerby checking them out, so she decided it was the perfect time for them to go into the water and splash around.

It ended up being a lot of fun and Alan forgot about how embarrassing it was to be at the beach in not only a frilly bikini but a buttplug and chastity cage. They had fun, and Roxanne got to make Alan look irritable to the guys watching them.

When they decided to take a break and head back to their towels, it was only a few seconds before the group of guys approached them and started talking to them. It started with them saying they looked like fun people and wanted to hang out.

Then when Roxanne told them it would be awesome, they grabbed all their stuff and set up next to them. That’s when the flirting began. There were seven guys now around them and six of them were constantly flirting with either Roxanne or Alan.

Neither of them could go more than a few seconds without getting complimented or having one of the guys offer to do something for them. Roxanne normally didn’t like when men were like that, but because it embarrassed Alan, she let it happen and even played into it.

A couple of hours go by and the group does all kinds of activities together, from beach volleyball where each team has three of the guys and Alan and Roxanne as the fourth member, to chicken fights where each guy gets to put Alan or Roxanne on their shoulders.

They even convinced Alan to sit still while they buried him and crafted a mermaid tail, which ended up with everyone including Roxanne taking pictures. It was now past lunchtime and Roxanne was starving.

She told the guys she had sandwiches if any of them wanted one, and they all took one and thanked her, but to them, it was just a snack. So a few of them offered to head out and get some pizza. Then another borrowed Alan’s cooler and went off to buy some ice cream for everyone afterward.

That left Roxanne, Alan, and the one guy who hadn’t been flirting with either of them. Alan was now enjoying the tamest moment he had today while sitting on his beach towel and taking in the sun, while Roxanne went to talk with the guy who stayed behind.

After a few minutes of talking to him, Roxanne walked over to Alan and sat down next to him. She then offered to make a bet with him. Alan was hesitant to make another bet, but it couldn't hurt to hear it out right?

Roxanne bet that if Alan walked over and asked that guy out he would accept. Alan rolled his eyes and said no way, he knew full well the guys had been flirting with them all day, it was obvious he’d say yes if he asked her out.

Roxanne turned her head like she was thinking and then looked back at Alan. She changed it, she now bet that Alan could walk over there flash his chastity cage, then ask out the guy and he’d still say yes.

Alan was shocked, there was no way he’d say yes after being flashed and finding out Alan was a guy. Roxanne then said if he didn’t say yes, she’d take him out of the chastity cage and remove his buttplug for the rest of the week.

But if the guy accepted, Alan not only had to date him, but he had to go home with him and let him play around with his butt plug. It seemed like a no-lose situation to him. So Alan accepted and got up. He walked over to the guy and stood in front of him.

He looked a bit confused and straight up said he had told Roxanne but he wasn’t interested. Alan thought that was great, he already didn’t want to date him, so this would only make him less likely to accept his offer of a date.

Alan with a smile on his face, pulled his bikini bottom to the side and showed off his cage to the guy. He seemed surprised and didn’t say anything. Alan then asked him if he liked what he saw and if he was up to going on a date with him.

The guy didn’t say anything for a minute, but then looked up at Alan and smiled. He said he didn’t even realize Alan was a guy. Alan said yeah, he was. The guy then stood up and accepted his offer for a date. Alan’s smug look then turned to shock.

The guy said he knew his friends had been flirting with them because they were pretty girls, but he was into guys, now that he knew Alan was a guy, one who just liked to crossdress, he was actually into him.

Alan slowly turned toward Roxanne who was lying on her towel with the biggest smile on her face, she winked at Alan and waved him goodbye as the guy got next to him and they started walking off. He then grabbed Alan’s butt and noticed he had something inside of it.

The guy laughed as he knew exactly what it was. He pushed on it a bit and Alan let out a soft quiet moan. The guy and Alan stayed closely together for the remainder of the beach day. When the rest of the guys arrived to find their gay friend with Alan, they quickly figured out his secret.

They didn’t judge and they all enjoyed pizza and continued to have fun. When the sun set though, Alan was led to his date's car, then he was in his date's house on his bed, all while having his date fuck his ass with the buttplug like it was a strap-on.

As Alan lay there he thought about all of this. Why was he committed to this bet so much? Surely he could just say no right, so why was he here, why was he doing this? Why did it feel so good and right?

Alan had no idea what Roxanne had in store for him tomorrow, but he knew whatever it was, he was going to have a very sore ass. The third day was over, but the third night was going to be long and sweaty, and he still had the rest of the week ahead of him.