Tails

Trenton caught the coin in the air and slapped it on the back of his palm.

"Tails," He said. I let go of a breathe I didn't know I was holding. Thank God. "Now can you please tell me what's going on?"

"Fine," I said. "The truth is the reason why I've been avoiding you and constantly turning you down is that I'm a lesbian. I don't like men. At least, not romantically."

"Bullshit. What about everything that happened these last two days?" He said.

"Let me finish," I continued. "That coin is magic. If you make a bet with someone when it's on your person they always accept, you always win, and they always cough up what you bet. I got it from my friend Abraham and have been using it ever since."

"Again, bullshit. Even bigger bullshit." Trenton said. "You're telling me if I said like, 'I bet you can't do a handstand right now and if I win you have to dress as slutty as you did last night from now on' you would really do it?"

"Deal," I responded. I instantly got on my hands and knees and tried to lift myself up. I just fell back on the floor, failing. "Fuck. Fine, you win."

"Ha ha, very funny Emily," Trenton said. "If you 'always win' why did I win our first bet?" Trenton asked. "About asking you out. Or just now with the coin flip. I guarantee you I would rather have you be my girlfriend than lie to me."

"Because it's not in your hand when you flip it. All the other powers are still in effect, but not the auto-win." I gestured to the coin. He held up the coin like he was putting the pieces together. In that moment I made my move and snatched it out of his hand. "Now, I've told you why all of this happened. If you don't believe me, you don't have to." I started to look for my bra has Trenton tried to put together what was going on.

"Look, Emily, if you don't want to date me fine," Trenton started up again. "But I'm honestly disgusted that you have to make up such ridiculous stories to avoid that when clearly something was here." I just groaned.

"I bet the next time you ask a girl out, any girl, she would say yes and you would never need to ask me out again. If I'm right, you believe me. Got it?" Emily said.

"Don't change the conversation," Trenton said.

"Got it?" I repeated.

"Fine," Trenton said. "But when she inevitably says no, you tell me the actual truth."

"Aye aye captain," I said. "Now I'm taking your toiletries to shower."

I rushed to class in my terrible dress. That was incredibly hard to do in high heels. I wanted to pick up my stuff from my house, but I was already running late.

I got many gawks and giggles showing up to class like I did. I just tried to ignore it and pay attention. At the end of my first class my professor, Dr. Cassidy, came up to me.

"Ms. Friedman. I'd appreciate if you didn't make a mockery of my class in the future." She said. I rolled my eyes. "Please come dressed prepared to work, not play. What you doing the comfort of your home should be between you and your playmates."

"Dr. Cassidy, with all due respect, I think I'm just fine. In fact," I picked up the coin from my desk and held it tight. "I think you could dress as skimpy and revealing as me all year and not get a single reprimand from the administration. If I'm right, you give me an A on our final project no matter what. If I'm wrong, you can fail me." I stuck out my hand and she shook it.

"I'll use my free period to acquire the proper garments," She said before walking off.

None of my classes were as bad as that one in terms of professors, but I did get constantly catcalled and even gropped once in a busy hallway. I didn't see who did it so I just moved on. I really regretted this dress.

When I got back to the car Amanda was asleep in the front seat. She had a pair of headphones on. I was more shocked by what she was wearing though. Or rather, what she wasn't.

The top of her ensemble was pretty basic. A small little chauffeur's hat on. I was honestly surprised to sex shop would have it. But as we move it down it got insane almost instantly. She had a ring gag in her mouth. Around her neck was a steel collar with a leash attached. Each of her hands was handcuffed to the steering wheel. The only thing covering her chest were two nipple clamps connected by a chain. I leaned over and saw what she was wearing as bottoms. A metal chastity belt that barely covered anything. And on her feet were incredibly tall ballet boots—up to her thighs—and once again with locks on. I knocked on the window a couple times but she couldn't hear me.

"Shit," I said. I pulled out my phone and called her. That woke her up. She opened the door promptly. "What the hell are you wearing?"

She just stared at me. Then she pointed to the dashboard. A key ring with five keys was on it. I picked it up and she turned the back of her head towards me. There, on the back of the ring gag, was a plate with a key hole in it. I tried a couple keys and got it on the third try. Then I took the ring gag out of her mouth.

"Thank you. My God that was uncomfortable," She said.

"Yeah. You know it's actually really dangerous to sleep with one of those," I said.

"Yeah but you said 'most degrading' and that fit the bill. I didn't want to disappoint." She said. Truly an insane statement, but I guess the coin made her think that she actually had to? "And honestly, I'm kind of shy about what I was listening to." This time I was the one to stare at her.

"Do I have to put in the employee policy complete honesty? Because you know what's going to happen if you don't tell me the truth." I threatened.

"Okay, okay." She took her earbuds out and paused the video on her phone. Then she held it up to me. "Bimbo subliminals" it read. "I had a lot of free time and I read online these could do some real damage."

I reflected on all I had done to Amanda. I had taken her from her home, pushed her to do insane embarrassing things, and now I was forcing her to fuck with her own brain. I didn't care that this was probably junk science, it said something about our relationship.

"Okay, new bet," I said. She just groaned.

"Again with another bet?" She said. I smiled.

"No, you'll like this one. I guess your favorite TV show, and you can have your free time back. Do whatever you want with it. Just make sure you remain slutty and available." I said.

"Okay," She sat up. "What's my favorite TV show?"

"You don't have one. You spend too much time reading. You manage two books a day on a slow day. Your favorite genre is historical biographies." I answered. I wanted to see how much I could get with the coin. "Did I get that all right?"

"Shit. Yeah, you did," She said. "And thanks for giving my free time back." I just smiled. Finally I was using the coin for what felt like some good. Amanda wasn't like my nemesis or anything. She was just fun to toy with. "Now can I ask you something?"

"Sure," I said. "What is it?"

"The key to the chastity belt is on that ring. I kinda put a couple vibrators in there to keep me wet. Can you please remove it so I can turn them off?" I just sighed.

I was exhausted from class so I just had Amanda take me home. I had her sleep in the couch, then I collapsed on my bed and waited for tomorrow to come.

The next day was Friday. The day of my date. An actual date I wanted this time. I got up with a burst of energy. I took a shower and blew out my hair, then moved to the closet. I started to take clothes out I never wore. A lace lingerie set that was a gift from a friend of a friend. Then I grab a button up shirt. I put it on but didn't button it up. Then I took a pair of beat up jeans and cut it so short with fabric scissors that it showed off half my ass.

I logically knew that I was doing this because of a bet, and that meant my mind wasn't in its right space. But it wasn't like the tension of the coin flip. I wasn't moving on autopilot. I legitimately thought these were the right choices to make, I just knew why I thought that. It was weird. Like when you know you're making a bad decision but you still go through with it.

I had enough time after class to go back and wear something more formal, but I knew no matter what it would still be slutty.

I woke up Amanda from the couch. I had her take a shower while I applied my makeup. I was very excited for tonight and nothing could bring me down.

Author's Note: Tell me if this wasn't long enough. Normally I don't feel bad about short chapters because I know for a fact another one will come up tomorrow but I don't know if I can keep pace when I have to write them from scratch now.

I was really surprised at the results. I was fully expecting heads and honestly felt bad about it because I posted a first chapter about a queer woman and then was cultivating an audience that wanted straight sex. So people putting their foot down and making it clear they didn't want that made me feel better. It did mean that I had to change plans though. I knew exactly where heads would go but less tails. Originally the consequence of the offhand bet Trenton makes in this chapter was going to be much MUCH steeper but people made it clear that they didn't like a story where Emily gets abundantly unlucky. She still gets her just desserts a little bit though.

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