"Let me get this straight, you want me to put that wig on and dress up for you?" Ian asked.
Katie giggled, "Well, technically, I guess. But it's more than that."
"Ya, I heard the first part of it, I just wanted to get the logistics down."
"So the deal is, whatever I wear for you, you'll wear for me later?"
"I dunno. How long do I have to wear it? And what if..." But Katie was already walking towards her make-up drawer.
Ian sat on the edge of her bed with a puzzled look on his face.
"Come over here silly!" Katie lured him in.
"Nah, this is too much." Ian shook his head.
"Don't be such a baby, my sister said her fiance does stuff like this for her all the time."
"Well, we're not exactly getting married."
"I know, I just thought it'd be fun."
"No, I'm serious, let's go do something else Kit-Kat." He tried to sound calm and not as weirded-out as he felt.
"Ian," She stopped what she was doing and looked at him plainly, "If you don't do this, I won't go to prom with you."
Ian's eyebrows raised. Why was she so adamant about this strange game? He thought for a moment to himself before replying, "Whatever, I didn't want to go anyways. Why do they even have it for college students? Isn't prom only in high school?"
Katie quickly thought up a new plan. She began to take off her clothes. "Come on, take off your shirt."
Ian still sat motionless but he had to admit his interest in her experiment began to build, the more clothes she took off.
She walked across the room to him and took his arm. Pulling him from off the bed she unbuttoned his jeans.
Ian was getting excited. He helped her with his pants and threw off his shirt in a hurry.
Standing in front of her in his underwear he was ready to start fooling around.
"Take those off too." Katie said sternly, motioning to his boxers.
Now he was completely naked and he took a step towards her.
Ian was frustrated but she had already gotten him hot so he went into the bathroom.
After he finished shaving his face Katie looked him over and came up close to him. Her body wrapped around him and she whispered into his ear, "I want you to shave everything."
Ian thought it was a ridiculous request but maybe he could slip past her suggestive dress-up game if he did this for her instead. And so he did.
But when he finished, Katie just told him to close his eyes.
Again, he did as he was told. The prolonging was making him all the more excited.
Suddenly he felt something on his lips. At first he thought she was about to kiss him but soon realized it was something much much different.
Ian's eyes opened but instead of protesting, he just let her do it.
When she had applied it, she taught him how to pucker his mouth so the lip gloss would spread evenly.
He knew what was next. But he thought if he could just get through her games quickly then she would do something for him.
Katie placed the auburn wig gently on his head and pulled it tightly down.
"How cute!" She squealed.
"Let's just get this over with." Ian said, beginning to feel the first stage of complete humiliation.
Katie continued on with his make-up. And Ian sat very still for her.
"Ugghh!" Katie exhaled, "You're gonna be the cutest girl ever!"
Ian felt butterflies in his stomach.
"Okay, all done! Let's go pick out some panties for you!"
And they did just that. Katie made Ian pick out his own pair. At first he kept saying "I don't care, you pick them..." But seeing as how that just wasn't going to cut it, he picked out a pair of LOVE PINK graffitied white cotton panties.
As he was slipping into them, he had a sudden shock and looked up at Katie with alarm and panic in his face. "What time does Melissa get home!?!"
"Oh, don't worry about her, she's gone for the next few days."
"Are you absolutely certain." Ian asked seriously.
"Ya, she's like the best roommate ever, she's never here and when she is here, all she does is clean." Katie reassured him.
"Here." Katie handed him a plaid micro-skirt.
He put it on quickly. Next, she gave him a pair of fish-net stalkings. He put them on a little bit slower and much more skepticly.
She gave him a shirt and some heels and began to get dressed herself.
Ian looked back over his shoulder at Katie after adjusting his clothes to fit more comfortably. She had a large grin on her face.
"What are you laughing at?" Ian snapped.
Katie didn't respond. She just kept on grinning, which made Ian mad.
"Seriously, cut it out. And why'd you put you're clothes back on? I thought we were gonna..."
Before he could finish, Katie spoke up, "Ya. We are, I'm gonna go get us some dinner first though."
"What!?!" Ian barked, "And I'm just supposed to sit her dressed like this till you get back!?!"
"Or..." Katie said with a twinkle in her eye.
"No way. No way. There is absolutely no way I'm going outside like this."
"Suit yourself. I'll be back in a little bit."
With that, Katie grabbed the keys off the coffee table and went out of the living room, down the hallway and out the front door.
Ian was dumbfounded. He couldn't believe that after dressing up for Katie she didn't do anything for him. He began to get very angry. Then he calmed himself down and reassured himself that they would fool around when she got back.
And so there he was. Painted up, shaved, and dressed like a girl alone in Katie's apartment.
Time went by slowly and he began to get very bored. What was taking her so long?
He went back into Katie's room and opened her closet. He took off the white tank-top he was wearing and decided to switch it out for another that he found. It looked like this was the top that matched the skirt anyways, he thought.
Another 10 minutes went by and he finally heard the keys turn in the front door.
Ian left Katie's room in a hurry and walked through the living room quickly. He almost fell because of the heels. "What took you so long?" He called out to her.
There was no reply but he heard the door close and the sound of Katie carrying in grocery bags.
"I decided to trade out that white top for this one." Ian told her as he began rounding the corner into the hallway. "What do you think...?"
As he turned to show Katie the outfit, he made what would become one of the most terrifying discoveries of his life. Melissa was standing by the front door with her mouth wide open.
Ian stopped dead in his tracks.
"Ian?" She managed to ask after a long and awkward silence. "Is that you?"
"Uh. Hi, Melissa." Ian responded as he fiddled with his skirt.
"What... What are you doing? Is Katie here?"
"No she's... Well, I thought she went out to get dinner but it's been like an hour and..."
Melissa cut him off. "Why are you dressed like a slut?"
Ian felt the butterflies again. He had nothing else to say.
Melissa saw how pathetic he looked. He was so shy and adorable standing there caught by her. She noticed that he kept trying to pull down his tiny skirt so she couldn't see his panties.
"Well, you do look kinda cute." She said.
Ian's face brightened up.
"Ya, I mean, it's a little trashy but you kinda pull it off."
"Can I uh, help you with those bags?"
"Oh, don't worry about them, I wouldn't want a sissy like yourself to break a nail or something." She teased him.
Ian moved out of Melissa's way as she entered the living room. He stayed for a moment and took a deep breath. Trying to collect himself and salvage what little dignity he had left.
Melissa called to him from the kitchen. "Are you sure she went out for food?"
"Ya, that's what she said."
"That's so weird because we just talked a few hours ago and she told me to grab some food on my way home for the party."
"Par-party!?! What party?" Ian tried not to sound shocked.
"Oh, you didn't know? I just figured thats why you were dressed like that."
Ian came into the kitchen. "What do you mean?"
"Ya, it's Katie's sister's bachelorette party here tonight."
Things became soberingly clearer for Ian in that moment.
He turned and rushed into Katie's room. Careful not to trip from the high heels again. He lunged for his jeans. But in the same instant heard a knock at the front door.
Melissa yelled to Ian, "I think the girls are here. You might want to put something more silly on. They'll get a huge kick out of it."
Ian was frozen. He listened to the door open and the sound of at least a dozen women pouring into the living room. He didn't know what to do.
Soon, Melissa stuck her head in. "Everything alright in here?" She asked as if he shouldn't have a care in the world. "I've got this great black lingerie set you should wear tonight. Everyone will love it!"
An hour later Katie finally came home. She walked into the living room in a huff where all the girls were chatting. "Sorry I'm late, I had to pick up the cake and there was this crazy line."
She put the cake down on the coffee table and her eyes scanned to Ian sitting on the couch. He was burning a hole in her with his bitter glare. "Oh, how precious!"
Katie's sister spoke to her from the chatter, "Ya! He was so great, we made him give lap dances and all. What a doll! It's all too funny!"
The other girls laughed in agreement and Katie sat down and joined the party.
The only one not laughing was Ian.
The night went on and the girls made Ian dance and preform for them. They slapped his butt and made him pose for pictures.
It was the most humiliating night of Ian's life.
That was until prom night...
"Please don't make me go inside dressed like this."