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Chapter 9
by Helforster
What do you do?
Go on the date
Did I really have to do this? I tried to pull down my dress, so it wasn’t showing off everything, but no matter how hard I pulled, it was going to look slutty. The worst part is, when I pulled, my arms **** my breast forms together. It looked like I was showing off my tits.
“You must be Kendra!”
That voice came from Brad. He wasn’t actually that bad looking. The loose fitting dress pants and the stylish button-up really suited him, and he clearly had been working out. His muscles were sizable, that’s for sure. As I looked him up and down, I realized that it looked like I was checking him out. The smile on his face told me he noticed my glares.
The silence was awkward, so I finally spoke up.
“Hi... I’m... I’m...” I tried to **** out, but the officer interrupted
“This is Kendra. She’ll be your date for tonight.”, He smiled.
I stuck out my manicured hand for a handshake, but Brad just grabbed it. He must’ve thought I was gesturing for him to hold my hand. I went along with it. This night would have to be over soon, so I just had to power through.
“So, where are you from?”, Brad asked as we walked down the street.
“Phoenix. I’m just here for the week.” I stated plainly.
“So a week in paradise?” Brad joked.
“Yeah... I guess so.” I was embarrassed, seeing the eyes of everyone we passed on me.
“Hey, I know you didn’t want to go on this date. Hell, I didn’t even want to go. But my brother is a bit of an authoritarian so you just kind of have to go along with it. So don’t feel pressured to do anything. We’re just friends here” He smiled, and it looked genuine.
For the first time in the day, I legitimately felt at ease.
We made it to a bar and got a seat. The place was darkly lit, very clearly a hot spot of the island nightlife. The music wasn’t blaring and overall, the atmosphere was good. I was still incredibly nervous, and I mean how could I not be? I looked like a slutty woman on a date with a decidedly attractive man. I was the target of so many looks, and my face was a permanent shade of red from the embarrassment.
“I understand. It can be embarrassing. Tell you what. WAITER!” Brad flagged down a waiter and whispered something into his ear. The waiter nodded and disappeared, reappearing soon after with a couple of cocktails. They were big with an orange-pink color. I took a sip and it tasted delicious.
“Yeah, these cocktails really help you get through the tough times. That’s what all the booze in them is for!” He laughed, and I laughed with him.
I needed the booze to keep the edge off, and before long, I was a few cocktails deep and beginning to have a really good time. I was dancing with several men on the dance floor, and soon I was dancing with Brad too. It was so much fun, and with the extra kick, I could feel my inhibitions leaving me. The embarrassment was washed away, at least for now, and I smiled for the first time since this whole debacle started.
The night went on, and as the bar was nearing close, me and Brad were sitting down just talking. Mostly about nothing, however, we found out that we had a lot in common. We were both huge hockey fans, and I laughed at him for living in the least hockey place on earth. He chided me back for the same. We liked a lot of the same movies, and all-around Brad seemed like a genuinely nice guy.
We moved to the dart board and started tossing them all over the place. It got stuck in the wall just as much as on the board, and I slurred together enough words to say, “I betyoucan’tbeat ME!” it all just blured together as it came out my mouth.
“Sure! Whatcha wanna wager?” Brad stumbled.
I didn’t even think as I blurted out, “If I win you buy the next round, if you win you can kissme”
At this point, I had been treated as a girl for so much of the night that I had begun to feel like one a bit.
“DEAL!” Brad stammered out.
After our little game, Brad barely squeaked out a win. I smiled, my eyes sunken and mostly closed, “Well, guessyou WIN!”
I leaned in, pursing my lips almost cartoonishly. Brad grabs the back of my head and pulls me the rest of the way in, sweeping me off my feet and pressing his lips against mine. It was probably just the **** talking, but it felt good. He didn’t feel forceful, and as we pulled away, he stood me up and looked me in the eyes.
“Hey, maybe it’s time we get you back to your place” Brad smiled.
“Yeahok” I slurred together.
Brad settled the bar tab and walked me out of the bar. I was barely able to get him the address of me and Kevin’s beach house, but he and I began to walk back.
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
- Tags
- Hypnosis, Misunderstanding, Crossdress, Halloween, Bet, Dare, Crossdressing, hormones, feminization, sissy, housewife, Stepford, Stepford wife, hucow, Maid, Fetish, Femdom, Thigh-highs, mistaken identity, mind control, manipulation, Accidental, Mr Handy, Vault, Fallout, Magical Crossdressing, Leather, Princess, Secretary, Fantasy, pokemon, Mindcontrol
Updated on Jun 15, 2025
by Mr Nice Guy
Created on Feb 1, 2018
by Dayeandknight
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