Best Girl Ch. 05

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The competition heats up.
7.1k words
4.48
48.7k
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Part 5 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 squinted at the bright lights as he strutted down the catwalk. He was in some kind of fashion show. Loud raucous music blared throughout the dimly lit room. Flashbulbs popped once, twice, three times, as he hit his mark and struck a pose. Walking back, he looked down and saw that he was dressed in a black lace merrywidow. Another flash and he found himself in a completely different outfit, a blue satin babydoll. He made another stop and turn. This time he looked down into the seats below and saw a familiar face, but he couldn't quite place it. The sudden instantaneous costume changes were disorienting but he started to walk with assurance after a while. Now he was wearing a brilliant pearl cami set. Flash. Now he was wearing a bustier with string bikini panties. Finally, walking with a slow confident stride, he placed the face of the woman sitting in the front row. The memories flooded back to him. Her name was Penelope and she was a member of the Alpha Phi sorority. She was running the "Best Girl" competition in which Todd and two other guys were participants with the hopes of winning a wild card bid to become a member of the Beta Phi fraternity. Todd had participated in various events as Tiffany while his buddies Jack and Chris were known in the competition as Jasmine and Candy. After the last event the score was tied at eighty points apiece.

Penelope's face was turned and she was talking to the person seated next to her. She turned to face Todd and the smile slowly sank from her face. Todd's latest outfit included a pair of sheer black stockings with a matching garter belt. He looked down and gasped. A run! The music came to a sudden stop with a screech. Bright lights came on. Penelope stood up and walked to a small staircase set at the end of the runway. The room was completely silent except for the sound of Penelope's heels clicking on the floor. She started up the few stairs and at the top she looked into Todd's eyes and shook her head. She held out her right hand palm up. Todd rolled the offending stocking down his leg and handed it over to Penelope. It was shaped like a long squashed donut. Still silent, Penelope opened her mouth and gestured toward it with her hand. Todd opened his mouth in return and Penelope shoved the rolled-up stocking halfway inside. Instantly everyone in the room started laughing. The music started up again and the lingerie fashion show recommenced as Penelope pushed the stocking in and out of Todd's mouth. Todd's attention turned to the laughing. The stocking. The laughing ...

Todd awoke with a shudder.

He said, "Ptuh. What's in my mouth?"

Peals of laughter surrounded him and as his vision focused he saw that Chris was on the bed behind him and Jack was directly in front of his face, standing at the edge of the bed. Jack's cock was semi-erect and glistened with saliva. Bringing his hand to his face, Todd confirmed that he was dribbling spit down his chin and that Jack had rudely woken him up from his dream.

Todd reached up and shoved Jack away and said, "What's the big idea?"

Jack said, "Oh, come on. Can't you take a joke? We were both up and Candy thought we should wake you up, too."

Chris, still giggling, said, "Hey, wait a minute. I said we should wake her up but I didn't say you should do that."

Jack said, "Details, details." Todd rolled out of bed in a huff and Jack said, "Hey, calm down. We better save our energy. Who knows what's going to happen today."

Todd was reluctant to concede the point but based on the way things were going today might indeed be a turning point. So far in the contest they'd dressed up like women and given handjobs and blowjobs to men. Early on they had even spent an evening on their hands and knees getting fucked in the ass by strapon cocks that the sorority pledges wore. Chris predicted that today Penelope was going to try to make them bend over while they got fucked in the ass by real cocks. They had all agreed to stick together to prevent this.

Todd said, "OK, but your hijinks aren't helping anything. Besides, you woke me up from a perfectly good dream." He slugged Jack playfully in the shoulder.

**********

Downstairs in the kitchen, Penelope, Samantha, and Kelly sat at the table. Various sorority sisters and pledges walked in and out of the door. Penelope consulted some papers and said, "OK, everything's all set. The guys are going to be here in a half hour."

Samantha asked, "Where did you get these guys?"

"Oh, the usual place. This was a bit of a special order though. The first bunch is just to break them in for an hour or two and then the real fun begins with the second group. Did you get the folding chairs ready?"

Samantha said, "Check."

"Perfect. Kelly, once they go in for their shower I want you to gather together their school uniforms and accoutrements and bring them to the bathroom. Have them get ready in there and don't let them come out until you get the signal. Meanwhile, Samantha will set up the chairs and get together the pledges to serve as audience. Once I bring the guys in we'll be all ready and then you can bring our girls back to their room for today's lesson: Anal 101. This is going to be great." Penelope rubbed her hands together.

Samantha hadn't seen Penelope this excited before. She asked, "Penelope, are they really going to go through with this?"

Penelope said, "Trust me, they're going to do whatever I want them to do."

**********

In the bathroom, Todd and Chris were going through their morning ablutions more solemnly than usual despite Jack's efforts to lighten the mood. That something different was going on was confirmed when Kelly brought in their school uniforms and told them to get ready in the bathroom. Before they'd always gotten ready in their bedroom. Todd slowly combed out his wig and pulled up his short pleated gray skirt. He buttoned his simple white blouse over a plain white bra with breast forms. Finally, he pulled on the long gray wool socks that completed his school uniform. When he was done he looked over and saw that Chris was just finishing dressing and that Jack was already finished. The door to the bathroom opened and Kelly poked her head in and smiled wide. She said, "Come on, let's get this party started."

Todd, Chris, and Jack followed Kelly back to their bedroom dragging their heels. There was a definite din coming from inside the room before Penelope opened the door. Once it was open Todd saw that at one side of the room sorority pledges sat in two rows of folding chairs. The usual chalkboard was set up for their lesson, but instead of the normal set of three school desks there was a padded mat on the floor. Penelope was dressed in her usual sexy school marm outfit and stood in front of the chalkboard. Three guys stood at her left dressed in large white robes.

Penelope took a step to the right and written on the whiteboad was, "Anal 101: A practical approach." Seeing the writing brought a bunch of guffaws from the audience of pledges. Todd looked around the room and his eyes caught Chris'. It had finally come to this. They were both surprised when Jack started to speak.

Jack said, "Miss Penelope, I don't think we're ready for this. I mean, maybe we should try this another time."

Penelope said, "Well, well, well. I think we have our first volunteer. Good show, Jasmine, you show them how it's done." She grabbed Jack and roughly pushed him to the mat. "Come on now, assume the position." The people in the crowd laughed.

Jacked struggled as Penelope forced him to his hands and knees. "Miss Penelope, I really think you should reconsider."

"And I really think you should shut your mouth, Jasmine. Hmmph, the nerve of these girls." She waved towards one of the guys in the robes. He walked over and started to position himself behind Jack.

Penelope raised the back of Jack's skirt and he blurted out, "We have a pact!"

Penelope stood still a moment and said, "Hold up. What's this about a pact?"

Jack said, jumbling the words together, "We all agreed. We're not going to let you do this to us."

Penelope smirked and said, "Is that so?" She looked at Chris and Todd and said, "And you two are in on this, too?" They both looked down at the floor and gently nodded their heads.

The people in the audience were silent. Penelope stood motionless for a few seconds and finally said, "Jasmine, I'm going to ask you this one time. Do you agree to continue today's lesson?"

Jack hung his head and said, "No, Miss Penelope. I'm sorry."

Penelope reached down and yanked Jack to his feet. She said, "Get out of this house." Jack looked around the room. "Now."

Jack said, "But what about..."

"Now! Did you hear me?" She shoved him. "Out. Out of this room. Out of this house. Out. Out. Out." She shoved him through the door. She walked over to the window and after a few moments she saw Jack come out of the front door, still dressed in his schoolgirl uniform. The skirt was still hiked up a little bit and his socks were askew. He got to the sidewalk and looked first down one way and then down the opposite way. Seeming to pick one at random, he slowly shuffled away from the sorority house.

Penelope said, "The nerve of some people." People in the audience started making noise and rustling around. "I'm sorry, people, it looks the show is canceled for today." With dejected noises most of the people got up out of their seats and left the room. Penelope caught the eyes of the three male models in white robes. "You too, boys."

Only Penelope, Samantha, and Kelly were left in the room with Chris and Todd who were still looking at the floor. Chris said, "What about us, Miss Penelope?"

"Yes indeed, what about you. I don't like all this business about pacts. If you had concerns about the contest all you had to do was come to me. But no, you had to play your little joke on me. Let me go all out. Hire the models, with my hard-earned money I might add! Set everything up. And then, oh no, we're not going to do it. Ha ha. Thanks for making me look bad. Thanks for wasting my money."

Todd said, "Are you going to kick us out too, Miss Penelope?"

She said, "Oh no, you're not getting off that easily. Jasmine out right refused me, but there may still be some hope for you two."

Chris started to open his mouth but Penelope said, "Shut up, Candy. I'm so mad right now I can hardly see straight. I need to step away for a moment or I'm going to do something we'll all regret." She looked at Samantha and said, "Keep them busy here for a while. I'll be back in a couple hours."

"What should we have them do?"

"I'm sure you'll think of something." Penelope exited the room and Chris and Todd turned to look at Samantha.

Kelly turned to Samantha and said, "What do you think?"

Samantha pinched her chin for a few moments and said, "I know, they should write lines on the board. Hmm, let's see, what should they write? Get up there and grab a piece of chalk!"

Kelly said, "Yeah, and maybe a little corporal punishment."

Once Chris and Todd were standing in front of the dry erase board holding a piece of chalk, Kelly walked up and pulled their skirts and panties down in the back so their bare buttocks were exposed. She grabbed the long wooden pointer from the tray of the chalkboard and gave each of them a test swat. Chris said, "Ouch."

Kelly said, "Keep quiet," and gave him another, harder swat.

Samantha said, "OK, this is your line. Write it very small so you can fit it lots of times on the board. 'I'm very sorry I embarrassed Miss Penelope. Even though I've taken many cocks in my mouth and happily swallowed down copious amounts of virile man juice, I was too ashamed to show how much I craved getting fucked in the ass by real men. I am a dumb slut.' How's that?"

Chris turned and started to answer but Kelly swatted him with the pointer and said, "Not you, ditz."

Samantha shook her head and said, "Candy has got to be the stupidest little bitch around. What do you think, Kelly?" She emphasized the last word.

"Excellent. Candy, this is your half and Tiffany, that's your half." She drew a line down the center of the board. "Now you two write your line nice and small and fit the whole thing across the top of your side. Then when you're done copy it all the way down."

Samantha said, "As you're writing I want you to concentrate on the words that you're writing and what you've done."

It took several more swats with the pointer for Chris to get his first line right. After that she waled on the two of them whenever she got the urge.

When the board was half-filled Samantha said, "OK, stop for a minute. You two need a break from writing." Chris and Todd look relieved and Kelly turned to Samantha with a puzzled expression. She said, "Break? I don't think Penelope will be happy you gave them a break."

"Well, call me kind-hearted." She gave each of them a couple of smacks on their slightly pink bottoms with her bare hand and said, "Bend over and grab your ankles." Chris and Todd grabbed their ankles. "All right, Candy, you first. I want you to say the line you've been writing, oh, fifty times. Kelly here will keep caning you until you're finished. Start now."

Kelly started to whack and Chris said, "I'm so sorry I embarrassed Miss Penelope." He stopped for a minute to think. Kelly swatted him three times, very slowly. He continued, "I'm a happy cocksucker. Uh, I sucked a lot of cocks and swallowed a lot of jizz, uh, cum. Oh yeah, warm man juice." Kelly gave him a particularly hard swat. "Ow! Um, I didn't want to admit how much I wanted to get butt-fucked by several hot guys. Oh yeah, I am a dumb slut."

Chris started to stand up but Samantha pushed him back down and said, "No truer words were ever spoken." She turned to look at Kelly and when their eyes met they both burst out laughing. After a few moments Samantha said, "That's one time, Candy, you've got forty-nine to go. I can't believe you've written the line over two dozen times and you still don't have it memorized. But you gave us a good laugh so you won't get any extra punishment. Warm man juice? Where did you come up with that?"

Chris thought for a moment and looked at Samantha from between his legs, his face upside down. He said, "Well, it was warm."

Samantha shook her head and said, "All right, keep going."

It took another half hour for Chris to get out the rest of his lines. He got the first sentence close enough and the last sentence was always perfect, but the middle sentence was constantly changing. He claimed to be a "happy cocksucker" and gave "happy blow jobs" and "gaily sucked cock" which caused Samantha and Kelly to erupt into peals of laughter. He "ate cum", "swallowed spooge", and "sucked down semen". Besides admitting he wanted to get "reamed by a bunch of hunks" and "bent over and fucked properly" there was a whole litany that involved a lot of handsome men admiring his ass and then fucking it and ejaculating into it which seemed to come out of nowhere.

Todd was struggling to keep his composure. Partly due to bending down and holding his ankles for so long, but mostly due to Chris' antics. If it weren't for the fact that Kelly was caning him during the whole time, Samantha would have said that Chris was hamming it up.

Finally Chris was done. Todd's turn took less than half the time and despite listening to Chris' wild variation of the line, Todd said it exactly right every time. When he was done Samantha and Kelly let them continue their lines on the board and only once in a while did Kelly get the urge to smack one or the other on the rear.

Penelope came back just as they filled the last space on the board. She took a glance over the board, quickly reading the contents. She said, "Nice work." She saw that Chris and Todd's skirts were pulled down and their buttocks were bright pink and gestured and said, "I'm not even going to ask about that."

Samantha smiled and said, "How are you doing?"

Penelope said, "Much better now. I've definitely calmed down. I worked out a little plan to recoup my losses. Things won't be set for another couple hours so why don't we take them back to that adult video store, the Pleasuredome and ..." She leaned over and whispered the rest. Chris and Todd leaned in to try and hear what she was saying, but Penelope pushed them away. She wore an evil grin. She said, "Don't worry. You made it abundantly clear your precious little bottoms are off limits." She started to laugh and Samantha and Kelly joined in.

**********

An hour later Chris and Todd found themselves back at the Pleasuredome, a store that sold adult videos and novelties. Two days previously they had spent time in the private rooms in the back taking pictures of men's cocks as part of the contest. Todd started heading in that direction as they went through the door, but Penelope grabbed him by the scruff and said, "Uh-uh." She shoved him to the main part of the store with Samantha and Kelly following him and Chris bringing up the rear. In the main part of the store Penelope halted them and roughly pushed Chris and Todd to their knees. She went to the counter and spoke with the clerk for a few moments. He handed her a small microphone on a long curly cord.

She keyed the microphone and her voice went over the PA system in the store. "Ahem. Attention, pervs. I've brought in a couple of hot schoolgirls for your perverted enjoyment. Naturally these girls need to keep their virginity intact so anything below the waist is off-limits. Please avail yourselves of their pretty little mouths. They will suck your cocks, swallow your cum, whatever." She handed the microphone back to the clerk.

The store was somewhat crowded because it was lunchtime. A murmur went through the store and guys started coming to the front of the store. When they saw Chris and Todd dressed in their school uniforms kneeling down they expressed their shock and surprise.

"Hey, what is this, some kind of joke? What are those pretty little ladies doing down on the floor?"

Penelope said, "Do I sound like I'm joking? Those pretty little ladies are here because they want to suck some cock. So either step up or step back."

The man stepped in front of Chris. Two other men went to step in front Todd. One said, "Hey, I was here first."

The other man said, "No you weren't. I got here first."

Penelope said, "Gentlemen, gentlemen. Please don't argue. There's plenty to go around. Here, you're on deck." She pushed the second man to the side a little. She gestured to the two men standing one in front of Chris and one in front of Todd and said, "When one of them is done you're next." A line of six men quickly formed behind the man on deck with a little jostling.

Penelope said, "All right, girls, let's get started. I know you're playing all innocent and virginal for these men so they'll get extra hot and bothered but now you're just being impolite. Each of you is staring a crotch in the eye. In situations like these girls like you have no choice but to unzip and get to work." She glared at them. Chris and Todd looked at each other for a moment and they both sighed deeply. Chris unbuttoned the pants of the man in front of him and fished his cock out. He took a deep breath and them put his mouth around the semi-erect member. Todd looked up into the eyes of the man standing in front of him. The man smiled down at him and undid his own pants. Todd reached up and gave the cock a few strokes and then put it into his mouth.

**********

After Chris and Todd had sucked off and diligently swallowed the loads of the first four men, a voice rang out from the front of the line.

It said, "Hey, Tiffany. Tiffany!"

Todd had a cock halfway in his throat and just as he heard someone shout his name the man whose cock he was ministering to started to come. Todd accidentally pulled the cock out of his mouth and it spurted all over his face. A quick cheer rang out from the men in line which had now swollen to a dozen.

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