Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes.

Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful. He would only try on clothing and shoes. In other words, he wouldn't risk putting on any makeup or nail polish or anything that couldn't be quickly removed (though he desperately wanted to) if someone were to enter his home. 

One Spring afternoon he was the first to come home. His mother was out of town on business, his father was out of the picture anyway, and his sister had soccer practice. He figured practice would run about two hours and his sister would probably not even stay at the house since Mom was out of town. So it was an opportunity for Jody...

He slipped on a new pair of his sister's pink panties and a matching pink bra. He posed in the mirror for a moment to bask in his joy. He always dreamed about being a Victoria's Secret model and strutting down the runway in the year's new lingerie and sky-high heels. Jody did acknowledge the fact that he was lucky to be short and very slender for his age. He was convinced that he could pass as a girl in public if he could practice with makeup and could muster the courage. Deciding to get a little more involved in the fantasy, he went into the closet to find his sister's sexiest pair of high heels.

He came out with a pair of four-inch silver strappy heels. He jumped up and swanned over to the mirror. Jody was extremely confident about walking in heels; after all, he probably wore them more often than most girls did. He couldn't help but think how great his toes would look if they were painted pink. He briefly considered the possibility. Unfortunately, he could not overcome the fear of being caught. He kept positive because he dreamed he would have the chance someday. What he didn't know was that day was coming very soon.

Jody was very aroused and this point and he laid down on his sister's bed. He let his hand trickle down his body and gently began rubbing his little clitty. He grabbed his stiff rod and started to masturbate. Just as he was really getting into it, Jody heard someone snickering. The fear Jody felt was so intense that he felt like he had been stabbed all over his body.

He looked up to see Chet Riley recording the incident on his cell phone. Chet, who was the age of his older sister, was the typical snide and falsely popular rich kid at high school. Nobody really liked Chet but they weren't actually brave enough to tell him of their dislike.

Chet went to the private school in town rather than the public one like Jody and his sister. He had been seeing Jody's sister on and off.
 
 "What are you doing?!" exclaimed Jody.

"I could ask you the same thing," said Chet smugly.
 
"Why are you in my house?"

 "The door was unlocked so I figured I'd let myself in. I came by to see Alex, but it seems that only her little sister is here."

Jody just sat embarrassed with nothing to say, waiting for Chet to give him further instructions.

"You see, Jody, there's two ways we can handle this. Both of them would be fun and entertaining in my opinion. However, only one of them would be any fun for you. The first option is that I can send this video to everyone at our schools and forever ruin your reputation. The other will get you off the hook completely. I assume option two is your choice? Of course it is. Well, you see my school's prom is coming up and I've yet to ask anyone to accompany me. And seeing as you are enjoying yourself so much, I figure you'll be that lucky lady."
 
 "Aren't you afraid that your friends will notice that I'm not a girl?" asked Jody, trying to find a way out of the situation.

"Not at all, Jody. Everyone at school is too afraid to challenge me on anything. I have dirt on every last one of them. Besides, with a wig and some makeup I think you'll make a very presentable lady."
 
"I can't do my own makeup and I don't own any wigs," said Jody, still thinking he could talk his way out of this.

"Didn't you hear me? I have dirt on everybody. I'll buy you a quality wig and find somebody to do your makeup. Do we have a deal? I'm getting tired of you stalling and I'm about ready to send this video out."

 "Don't! I'll do it! Just let me delete the video on your phone afterwards." 

 "We've got a deal! Don't be worried. Worst case now, everybody catches you wearing a prom dress. The other way, everyone would have seen you stroking it in your sister's underwear! Just be thankful that I've given you a chance to make it a fun experience."

Chet walked by Jody as he was leaving the room.

"Oh, one more thing," said Chet as drew closer to Jody and grabbed his pantied ass, "I'll still send that video out if I don't get lucky on prom night."

Chet left.

Jody sat bewildered by what had just happened. Yes, he was worried about what he was being forced to do. But he'd be lying if he said he wasn't a little bit excited. He was finally going to get to live his dream of being a girl. Jody hoped it wasn't too obvious that he was excited to get all dolled up for prom and to explore his curiosity with Chet. However, it was obvious.

The evidence being Jody's rock hard erect shaft.