Prom is a Bitch

byToniNewellcd©

Sadly, this is not a true story... just a novelization based on several online roleplays I've had over the past year or so. All characters are fictional, all scenarios are made up. My roleplays tend to begin more romantic and silly, and end with sexier scenes.

CHAPTER 1

My name is Anthony Newell, or as I prefer to be called now, Toni. Back when this story began I was just Anthony. Puny, effeminate Anthony. I don't know what sort of screwed up genes my parents gave me, since my mother is 5 feet 6 and a physical fitness trainer, and my father is 6 feet tall, even, and a former high school football star. Their eighteen year old son hasn't grown an inch since 8th grade. That's right, I'm 5 feet, 3 inches. And 115 pounds soaking wet.

At least my parents aren't jerks about it or anything. Dad can't play football with me, but we share a passion for music and comedians. Mom is much more physically fit than I am, but we jog every morning together. We all get along, despite them both being gone pretty much every weekend on business trips. It's taught me independence and household skills. I'm a fabulous cook now, and my best friend Kyle comes over for dinner and usually stays the whole weekend.

Now let me tell you about Kyle. Kyle and I have been best friends since he moved across the street from me 12 years ago. On the surface we don't have much in common, me being short and effeminate, him being 6 foot 4 and one of the school's star soccer players. My shoulder length dark hair compared to his short wavy blonde cut. But aside from our glaring physical differences, we share an interest in old Nintendo games and bad sci-fi movies. And since he's coming over for the weekend, I have no doubt we'll be watching plenty of B films and playing quite a lot of Mario Kart.

And so i sat, practicing my Mario Kart skills before he came over to solidly kick my ass. I heard him open my front door and walk into the living room, sitting down next to me. He looked exhausted.

"Hey Kyle... what's up? You look stressed out." I hand him a controller.

"Hey Anthony... long story. You know Amber right?"

Amber is Kyle's girlfriend. We hate each other.

"Yeah, unfortunately. She isn't moving away is she?"

Kyle rolls his eyes, used to my jabs at her. "No, although now I wish something like that happened... She dumped me! Two weeks before Prom, she dumps me! She KNOWS I already bought tickets and dinner reservations, and she has the nerve to just kick me to the curb like that!"

"Bitch" is all I can say.

"You're telling me. And guess who she's going with instead?" Before I can answer, he rails on. "She's going with FRANK, of all people!"

I look at him, astonished. "Frank Smith? Like, the other star on the soccer team Frank? Your big rival for the soccer scholarship Frank?"

He smacks his forehead and puts his face in his hands. "Yes! That Frank! Urgh it pisses me off so much... and to add insult to injury, I rented a limo yesterday for Prom night. That, plus the tux rental, dinner reservations, and the two tickets has me for a couple hundred dollars." I pat him on the back slowly, not sure what to say. Kyle's been saving up for a new car stereo, and hadn't even wanted to go to to Prom, only agreeing to go for Amber's sake.

Kyle sits in silence for several minutes, staring at the ceiling. I'm not the best at girl issues like this, especially with my mutual hatred of Amber. As he sits and i watch him concernedly, i see his expression change.

Oh no.

I've seen that expression before. This is the look in his eyes he gets before we nearly get arrested. The look in his eyes when he decides he wants to go cow tipping.

"Anth... you remember that Halloween party a couple years ago?"

FUCK

"Um... Yeah..."

"The one where you wore a cheerleader outfit, and all those guys hit on you before they realized who you actually were?"

"DAMMIT yes I remember! What's the point you're trying to make dude?"

"No homo man, but you looked damn good as a girl. This is going to sound extremely strange, but would you consider being my date to prom?"

All I could do was just sit there, gaping at him. "Wh-what... Why... The hell... Do you have any idea what you're saying?!?"

"Easy, dude! Just think about it. Whether you like it or not, you make a pretty convincing girl. It'd be completely free for you, I already have tickets and everything. I get a hot girl on my arm to show Amber up, you go to your own senior prom, which I know you want to do, no matter how much you say it'll be lame."

I hate when his arguments are actually kind of convincing. If I was a normal person, I'd refuse this ridiculous offer and laugh it off as him joking.

But I'm not really that normal of a guy. In fact, something deep within me, something I can usually keep hidden, wanted nothing more than this.

You see, I'm a crossdresser. Aside from that Halloween party a couple years ago I've never taken is public. But this offer of going to prom, fully dressed, in order to show up another girl? It pulled on me. I knew I'd give in eventually, as much as I hate to admit it.

Seeing my hesitation, Kyle sighed. "You know as well as I do that I hate to do this but... Don't forget that you owe me, Anthony."

I wince. "I thought we agreed we'd never bring that up again."

"Be my date to the prom in a couple weeks, and it never happened in my book."

I know when I'm beaten. "Fine. But like you said, I'm not paying for ANYTHING. Which means we have to go dress shopping tomorrow, on your dime. That clear?"

He nods, trying to be serious but betrayed by a large grin on his face. "Shopping trip tomorrow morning then?"

"It's... a date."

To be continued!

I know how the rest of the story will go, but if anyone has suggestions or criticisms please feel free to comment and let me know. Chapter 2 will be up in a couple of days or so.

Report Story

byToniNewellcd© 25 comments/ 60400 views/ 17 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartBrendaNW, hawken333 and 15 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by BrendaNW12/25/13

please do chapter 2

please finish chapter 2 .. and maybe more.. you are imaginative and write very well and have me hooked.. I am just like Anthony :)

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 25 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel