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CYOTF (New)

A Vacation As Nikki

added 7 months ago TG Male to female

“Okay, and remember…..I brought you along to keep Jacob’s brother occupied. I don’t care if you kiss him, flirt with him, heck, let him feel you up…..just don’t have him coming back here to the hotel room. We’ll be…busy.” my sister said, smirking broadly as my mouth fell open and a too feminine for comfort huff escaped as I gaped at her. “Firstly, I’m not do—doi—doing—-no way!” I said, crossing my arms and huffing again. Of course, given that I was wearing a tight little red dress, heels, and, as far as anyone looking on from the outside would have been able to tell, a teenage girl pouting after her sister had teased her, it didn’t exactly send out the masculine vibes I was hoping for.

For about the millionth time I wondered how my sister had talked me into this. She’d met Jacob at a work convention, and he’d asked her out for drinks afterword. Working in sales, she was awfully good at convincing people to do crazy things they never would have agreed to otherwise. I was proof positive of that—in fact, that was what had gotten me into this mess in the first place.

FOUR MONTHS EARLIER—HALLOWEEN

I faked a perky smile as the cameraman took our picture, the blinding flash causing spots to appear in front of my eyes. I blinked rapidly to clear them as the cameraman, already moving on, called “looking good, ladies!” Amanda grinned at me and rustled her pom-poms. “See little sis, I told you nobody would catch on.” She said, laughing again as I grumbled. It was a bit of a blow to my ego how easily she’d transformed me into “Nikki.” When she’d suggested I come along to her work’s costume party as a cheerleader—a FEMALE cheerleader—I’d balked. “Why can’t I just be a football player?” I’d asked. Amanda had explained that there was a prize for the most convincing costume, and that with her technique there was no way anyone would guess I was a guy. I grumbled a lot more, but with the promise of a new video game system at the end—and that nobody would find out unless we told—I was sold.

The transformation—the expert application of makeup and hair extensions, the attaching of uber realistic—and unnecessarily large, in my opinion—breast forms, the shaving off of all body hair—-went by faster than anticipated. Even I didn’t recognized the dark haired girl staring back at me in the mirror. I’d always been on the slight, short, and skinny side, but this was just nuts! Amanda taught me how to pitch my voice in a feminine manner—another thing easier than I would have wished—and before long I was dressed in the black and red cheerleading costume Amanda had bought for me, rustling my pom poms like I’d seen the girls at school do a million times.

I’m not sure whether to be relieved or embarrassed how easily the night went at first. Amanda introduced me to everyone as her little sister Nikki, and not even her female coworkers seemed to notice anything strange. Some of the guys were real creeps; there’s nothing like a guy old enough to be your father talking to your chest to bring out your embarrassment at being a guy. “Welcome to the club.” Amanda had told me with a wry look when I’d complained about the guy, who I guess was a vice president or something after he’d wandered away.

The rest of the night had gone smoothly enough….right up until the end. One of her coworkers, a guy a couple years older than me in a Gretzky jersey, had had a bit too much to drink. I’d been standing in a corner taking a breather from keeping the act up when he’d lurched over. “Hey babe…..you’re hot. How about a kiss?” He slurred. I opened my mouth to object…..and he took it as an invitation, lurching on in. I managed to break the kiss after a few seconds of frantic squirming, and, to their credit, some of my sister’s other coworkers firmly escorted him out of the room, but the damage was done. The last thing I wanted was any more attention, and rather than drop the charade we’d decided to keep it a secret. It wasn’t like Amanda talked much about her personal life at work anyway, so it should be fine…..I hoped.

ONE WEEK AGO

When I got home from the gym I realized something was up. Amanda had a strange look in her eye, and was sitting in a chair in the middle of the living room. “Nick—or rather, Nikki, we need to talk.” She said……


What do you do now?


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