Best Girl Ch. 01

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A contest for three guys desperate to get into a frat.
6.8k words
4.39
98.8k
54

Part 1 of the 7 part series

Updated 09/22/2022
Created 12/09/2004
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To be read by adults at least 21 years of age.

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Todd sat in a low chair in a hallway, a makeshift waiting area at the Alpha Phi sorority house. It was early afternoon and the house was mostly deserted. Another guy had arrived about fifteen minutes before and sat down next to him. A couple of girls had passed through the hallway about ten minutes earlier, but so far no one had gone in our out of the room he was waiting outside of. A third guy entered the hallway and walked over to where they were sitting. He checked his watch, stared at the door for a moment, then finally sat down.

"Are we all here for the same thing?" He asked.

Todd and the other guy stared at each other and then back at the first guy. The other guy asked, "I don't know, what are you here for?"

"Well, I rushed the Beta Phi fraternity and I didn't get a bid. I got a note that there was going to be another chance to make it in. I'm Jack." Jack was had a trim muscular build and short black hair.

The guy next to Todd struggled up out of the chair and stuck out his hand. "Hi. I'm Chris. I guess we are here for the same thing." He shook Jack's hand. Chris was several inches taller than Jack and thin. He had shaggy medium length sandy blonde hair.

"I thought you looked familiar," Todd said. He got up and shook hands with both Chris and Jack. "Hi. Nice to meet you. I'm Todd." Todd was just an inch shorter than Jack and was even skinnier than Chris. He had medium-length brown hair.

"Oh yeah, now I remember," said Chris. "You were at the rush party."

"Yeah, I didn't make it past that."

"Me neither." Chris looked at Jack. "Hey, I don't remember you at all."

"You sure? Well, I didn't even make it to the end of the party. Have you guys knocked on the door yet?"

"Well, no," Chris answered.

"I'm sure they'll let us in when they're ready. Maybe more guys are coming."

"Nonsense." Jack knocked on the door. "Hello?"

The door opened and a girl stepped out. She was tall and thin with glossy black hair that she was wearing up with an elaborate fastener. She wore a tight light gray business suit with a very short skirt. She carried a clipboard which she consulted. "Are all three of you here?" She looked up. "Chris? Todd? Jack?" Each guy responded to his name. "Very good. Gentlemen, please come in."

Three chairs were set up in front of a large desk. The girl walked around and sat behind the desk while the three guys sat in the three chairs. There was another girl sitting in a swivel chair in the corner of the room. She was slouched down, idly turning the chair to the right and left. She had on tight low cut jeans and a little clingy white tank top. She had curly blonde hair and when the first girl walked by she rolled her eyes. "Sheesh, Pen. Can't we go to the beach or something?"

"Patricia, now just hold on a minute. I've got business to attend to."

Trish snorted in laughter. "All right, Penelope." She dragged out each syllable of the name. "I'll just sit here with my thumb up my butt."

All three guys were looking over at Trish and they chuckled. "Gentlemen, please. Direct your attention to me." All three quickly looked her way. "We're here for a very serious matter." She consulted her clipboard again. "Each of you tried to rush Beta Phi and didn't even make it into the pledge class. As you may know, this sorority, Alpha Phi, is the sister sorority of the Beta Phi fraternity. I'm the chair of the joint Pledge Oversight Committee and in reviewing your records I decided to give you another chance."

The three guys looked at each other and smiled.

"Cool."

"That's great."

Penelope continued. "Now, there's only one slot open so I've decided to hold a contest between you three to see who is awarded the slot."

"Wait a minute," Chris broke in. "Doesn't the rush end this coming week?"

Penelope glared at him. She took a breath and said, "Yes, the same as the contest. Now if you'll please refrain from interrupting me."

"Sorry."

"Understand that because you're on the accelerated track it may be an intense week. Do you boys understand that?"

"Sure."

"Yeah, of course."

"All right. Here is the standard pledge contract." She handed each of them a clipboard with a stapled packet of papers on it. "Look it over carefully and sign it. Then we'll get everything started."

Jack flipped through the pages quickly and signed the last page with the pen that was attached to the clipboard. He looked at the other guys and said, "It's the standard Beta Phi pledge contract. I signed the same thing last year when I made it further along in the process."

Chris said, "This is your second time? Try number four for me. This is my last chance to get in. If I don't I'll never hear the end of it from my father. He's a Beta Phi and made pretty damned sure I'd better make it, too." He flipped to the end and signed the last page of the pledge contract. "What about you, Todd?"

Todd has also turned to the last page and signed his name. "Well, it was my first time rushing, but I made it a personal goal of mine to make it and I don't like to fail. I'm so glad we get this second chance." The three guys passed their clipboards back to Penelope.

"Yes, yes," said Penelope. She stood up. "It's all very touching. If you didn't already guess, I'm going to be your pledge master, Miss Penelope to you. I don't want you to speak unless you're spoken to and you're to follow my instructions to the letter. We haven't yet finished all the details of the contest but we've got a room upstairs where you three will stay this week." She walked to the door and opened it. She stuck her head out the door and yelled out, "Pledge!"

A girl came running down the hallway at breakneck speed and stopped in front of the door. "Yes, ma'am?"

"Pledge, show these guys to the room you were getting ready earlier today."

"Yes, ma'am."

She looked back at the group of three guys and said, "You guys have to understand the pecking order around here. In this house we have sisters and pledges and even the pledges are above you because they're real pledges. Is that going to bother you?"

Chris and Jack said, "No."

Todd said, "No, Miss Penelope."

Penelope put her thumb and forefinger under Todd's chin and smiled. "I think there's hope for you after all. Now I'm taking a chance on you guys and you better not make me look bad. All right, go already."

The pledge led the guys down the hall. Penelope stepped back into the room and sank down into the chair behind the desk.

"Pen, what are you up to?"

"What? Just doing a little public service. You heard those guys, I'm going to fulfill someone's lifelong dream."

"I'll bet. You're just pissed you didn't get to be the pledge master for us this year. After what happened last year you're lucky you're not banned permanently. Who'd you cozy up to over at Beta Phi to pull this thing off?"

"Never you mind. And I'm going to do things right this time. I promise."

"Whatever you say."

"Now come on. Let me change out of this monkey suit. We have a couple hours to kill and I'm at your disposal."

Trish got up out of the chair and twirled her finger sarcastically. "Yippee."

**********

Later the guys were hanging out in their new room. Todd was on the king-size bed. It had a hot-pink comforter on it. Jack was laying on the couch which was under the window and Chris was laying on a shaggy throw rug on the floor in front of the bed. Off to the side there was a vanity with a large mirror. The room's decor was pink and fluffy and the guys looked out of place. The door opened and Penelope walked in followed by three other girls. She had her hair down and it was very long. She was wearing white pants and a black halter top.

"How are you guys doing?" She didn't wait for an answer. "Good, good. I'm sure you're anxious to get things started. Let me introduce you to the three pledge captains. Kelly, Samantha, and Donna." She gestured at each girl as she said their names. "We're so proud of this year's pledge class." She reached over ruffled Samantha's hair. "We're having a party tonight, a costume party in fact. We're holding a best costume contest for you three guys. Kelly, Samantha, and Donna are heading up the three teams who are going to design a costume for each one of you. Their job is to make the costume and your job is to wear it. Understand?"

Chris, Jack, and Todd nodded.

"Good. Now this is very important to them so don't mess it up. I don't want to hear any complaints. From them or from you." She glared at them. "Donna, take him," she gestured at Jack, "into your room. Kelly, take this one," she gestured at Chris, "into the bathroom." She looked at Todd. "You're staying in here with Sam." She looked back at the girls. "Get your teams together and get to work. You only have an hour and a half. I want to see some fantastic costumes or I'm going to be disappointed."

Everyone went out the door but Todd. Samantha returned a few minutes later with two other girls. Samantha had the same long glossy black hair that Penelope had and had a lot of the same features but was a couple inches shorter. One of the other girls who came in with her had brown hair and the other was a dirty blonde. They each were holding a large shopping bag. They came in and shut the door. Todd tried to say hi but they didn't respond to him. He said, "Well, do you guys need any ideas for a costume? I was a really good devil one year."

Samantha looked at him and said nothing. She turned to the other girls and said, "I think I guessed the right sizes. What color hair do you think?" She reached into one of the shopping bags and pulled out a strawberry blonde wig. "This one?"

The brunette said, "Yeah, that's perfect." Samantha put the wig on Jack's head.

Samantha reached into the bag again. She asked the other girls, "Now what do you think of this skirt."

Todd was feeling uneasy and said, "Hey, what's that for? I'm not wearing a skirt. This wig was fine when I thought you were making me into a rock star or something, but I'm not dressing up like a girl."

Just then the door opened and Penelope walked in. "How are we all coming along here? Making progress I hope." She looked Todd over. "And what are we doing here?"

Samantha answered, "Well, I had this idea to dress him up like a girl. You know, like they do sometimes on TV?"

"Yes, yes. I see it. He'll make a very pretty girl. Good work, Sam. Make sure you emphasize those full lips."

"Yeah, but I don't think it's going to work out."

"Oh? Why not? I'm sure you can make Todd here into a very convincing girl."

"I think so, too, but he doesn't want to do it."

"Oh no? Is that true, Todd? The very first thing we ask you to do and you're not going to do it?" She put her hands on her hips.

Todd looked down at his feet then back into Penelope's eyes. "Not exactly. I was just taken by surprise. I wouldn't make a very good girl. I'd look like a dork."

"Come now, this is a costume party. You're supposed to look like a dork. And anyway, I have the utmost confidence in Samantha here. Why, I bet she'll do such a good job that you can pass as a real girl." Samantha smiled at the compliment. "Now are we going to forget this talk of quitting?"

"I never said anything about quitting," Todd answered. "I just had to get used to the idea."

"Excellent. Now I don't want you to give Samantha any more problems. You need to take each challenge we present you with and give it your all. If you're going to get dressed up like a girl, well, you better be the best girl you can be. Understand?"

"Yes, Miss Penelope." The other girls snickered.

"All right, I don't want to have to come back here. I'll see you at the top of the stairs when you're all done." Penelope left the room and closed the door behind her.

Todd said to Samantha, "You didn't have to go and rat on me."

She answered, "Quiet, you. We don't have much time and we have a long way to go. Just stand there and let us work." She grabbed the bottom of his T-shirt and lifted it up over his head. Then she reached over and unsnapped his jeans.

"Hey!"

"Listen, do you want me to go get Penelope again? I didn't think so. I don't want to hear another thing from you. You think it's easy being a girl? Well, it's a lot of hard work. And we haven't even started yet." She pulled down his jeans and he stepped out of them. Then she pulled down his briefs and he was standing there in front of the girls completely naked. She took off the wig and set it aside on the vanity.

"Ah, a fresh canvas." The two other girls chuckled. "You two, get serious. We have a lot to do." She emptied out one of the shopping bags onto the floor and put Todd's old clothes into the empty bag. She picked up an electric razor and handed it to the brunette girl. "Here, Vanessa, you get started on the legs." She picked up a different razor and handed it to Todd. "Here, you better do your face again. Get as close as you can." She looked at the other two girls. "I've got the hard job." She went into another one of the bags and pulled out what looked like a very small crock pot and placed it on the vanity and plugged it in.

The blonde asked her, "Wow, are you going to do a Brazilian on him?"

"Not quite. I thought I'd leave a little patch up front."

"Cool. I've got to see that. Where are you going to do it?" She looked around the room.

"Good question." She held her chin between her thumb and forefinger. "I know, over the end of the couch."

"OK. I'll be done with the legs in a few minutes. Then I'll use the clippers on the pubes and I'll give you a hand with the yanking. The wax'll be ready then." Todd's eyes went wide.

"Thanks, Kaitlin. Vanessa, why don't you look through these clothes we brought and put together an outfit. I want something that will draw attention. Not too slutty, though."

"OK."

A few minutes later Todd found himself bent over the arm of the couch with his legs in the air, bent at the knees. His head was laying on the seat of the couch. Samantha and Kaitlin were putting hot linen strips laden with wax on not only his crotch area but also around his asshole. When they cooled they were unceremoniously pulled off as Todd howled in pain.

Samantha said, "Oh you big baby. I bet you never gave it a single thought as you drooled over your private copy of the Sports Illustrated Swimsuit Issue." Vanessa had smaller strips and was using them to neaten up Todd's brow area.

Todd wasn't exactly sure when things had gotten out of hand. The pain was bad enough but even worse was the embarrassment he felt. He supposed he was physically stronger than Samantha. Well, he could put up a pretty good fight at least. But he had easily fallen into doing just what she said. He looked over at the end of the bed where Vanessa had laid out the clothes he was going to wear - a pair of long white stockings, a black garter belt, a matching black lacy bra and pair of high-cut panties, a short black skirt, and a long sheer white blouse.

Samantha noticed him looking and said, "Oh, I know you're anxious to put on your pretty things. We'll be just another minute here." Todd blushed and thought to himself that it was just one night. If he could get through the waxing he could get through anything.

"There, all done." She helped Todd to his feet and gave him a little slap on the ass. He stretched out a crick in his back. Samantha grabbed a bottle from the vanity and squirted something out of it onto her hand. Then she reached down and rubbed it onto Todd's crotch where his hair used to be.

"Hey, now," she said. "None of that. This is just to make you feel a little better, not that much better."

"Sorry."

"Now squat down a little and let me rub it on the other side. Doesn't that feel good?"

"Yeah, kind of soothing."

"I must say, you've been behaving very well. Now can we continue the trend and get you into your clothes without a big fuss?"

"Sure." The truth was, Todd felt really nervous around the girls when he had no clothes on and anything would be an improvement, even a skirt and panties.

The girls dressed Todd, starting with the bra and panties. Samantha put breast forms into the bra and when she was done she stepped back and all the girls gave him the once over. "Not bad if I do say so myself. Turn around. There, that's nice. His ass looks nice in those panties now that the hair's gone. Don't you agree?"

"Yeah, great," said Kaitlin.

Vanessa said, "I want to see how he looks with the stockings on."

Samantha said, "Ooh yeah." Vanessa helped Todd into the left stocking then Kaitlin helped him into the right one. Samantha slipped the garter belt around his waist and fastened the hooks in the back. Then Kaitlin and Vanessa attached the stockings.

"That looks great." Samantha slapped Todd's ass playfully a few times. "He's so cute!" She looked into his face. "Below the neck at least. Now you put on that skirt and blouse yourself. Do we have to do everything?" Todd did as instructed and looked down at his chest. He could see the black bra through the shirt. He had breasts! "Sit down here in front of the mirror and we'll do your face." Todd sat down in front of the vanity.

"Penelope was right about his lips. Let's build around them." She glanced at her watch. "Don't hurry, but there's not all that much time left. Let me slip upstairs and change for the party and I'll come back and finish up if you're not done. Then you two can change."

"OK."

Kaitlin and Vanessa applied makeup to Todd's face, first a foundation then a little hint of blush. After picking up several tubes of lipstick and holding the stick against Todd's face, Vanessa finally decided on a color and delicately applied it to his lips. She handed him a napkin, "Here, press down on this. That's good."

Kaitlin gave him a little eye shadow, then darkened his brows and brushed mascara on his lashes. "He's really shaping up," she said.

"Yeah," Vanessa agreed. "I though this idea of Sam's was half-baked but now that we're almost done it looks positively inspired."

Samantha walked back into the room.

"That was fast."

"Yeah, I had everything all laid out. You two go on and change. It looks like the face is all done." She picked up the wig and put it on Todd's head. "I just need to brush this out a little and we'll be ready."

"OK, Sam. See you at the party." The two girls left the room.

"I brought you some shoes. They're mine so be careful with them."

"Thanks." He slipped into them, a pair of simple black pumps with a modest heel.

"Almost a perfect fit. I didn't think you'd be able to handle high heels."

Penelope came back into the room. She said, "Well, well. Doesn't she look nice? Great job, Sam."

Samantha smiled and said, "Thanks. It was hard work, but I think I did OK."

Penelope walked over and unplugged the wax pot. "Wow, you went all out." She looked at Todd's face. "Now I see what you did."

"Not just there, either."

"You don't mean..." She looked at the wax pot again, then to Todd's waist. "A bikini wax?"

"Front and back."

Penelope snorted in laughter and slapped the side of her leg. "I've got to see this. Lift your skirt." She yanked Todd's skirt up. "Oh, that's just precious. And turn around. That's nice. Bend over a bit, dear. There, that's it. A very thorough job. Did she put up much of a fuss?"

"Well, she made a little noise, but that's understandable. Overall, I think she behaved herself." She patted Todd on the head. Todd raised his hand.

Penelope said, "Yes, dear?"

"Miss Penelope, can I ask why I had to get waxed? I mean I can understand my face, but why down there? You can't even see any of that with my outfit."

"Sam, why don't you tell us."

"Well, I don't like to do anything half-assed. I took this as a personal challenge. There's more to being a girl than just putting on a skirt. I wanted to go all out."

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