Best Girl Ch. 06

Todd said, "Oh, hi," and turned to Penelope and said quietly, "What's he doing here? He doesn't know about me."

Penelope responded in a loud voice, "Don't worry, Tiffany, and don't be embarrassed. We told Reggie here all about you, isn't that so, Reggie?"

Reggie said, "Boy, howdy. I didn't know you were a dude, but that's cool. You still gave me the best blowjob I ever had and as far as I'm concerned you're the prettiest girl I ever seen."

Penelope and Todd looked at each other and shrugged. She said, "Well, Tiffany, better get to work. I don't actually plan to give you explicit instruction unless it's absolutely necessary. I'll just let your natural instincts take over."

Todd took Reggie by the hand, lead him over to the bed, and sat him down. He took off Reggie's shoes and socks and gently pulled off Reggie's T-shirt. He had Reggie stand up for a moment so he could pull down his jeans and undershorts, then had him sit back down again. Todd knelt down in front of Reggie and worked Reggie's cock for a few strokes until it became semi-erect and then put he put his mouth around it.

Penelope put her hand on Todd's head and said, "That's a good girl, Tiffany. You want to get that cock nice and hard before it goes into your ass. From what I understand you're intimately familiar with that cock. Didn't I do a nice thing for you? To reduce your anxiety?"

"Mmph. Yes, Miss Penelope. Mmph."

After a few minutes Penelope said, "OK, enough of that. Why don't you both get up on the bed." She handed a small bottle of lube to Reggie. And why don't you leave your pretty uniform on? It looks so nice. You don't mind Reggie, do you?"

"Whatever you want, miss. It's your show."

"Here get on your hands and knees like this, Tiffany. We'll just pull down her panties mid-thigh like this and flip up her skirt like so. There, you have ample access to her ass that way."

Reggie said, "Gee, thanks. And what do I do with this?" He held up the bottle of lube.

Penelope shook her head and said, "Put a glob on her asshole. Yeah, like that and rub a little bit into the head of your cock. That's good. Now go to town."

Reggie pressed his cock against Todd's asshole. He leaned over and whispered into Todd's ear, "Do you want me to start now?"

Just as Todd nodded his head Penelope reached behind Reggie and pushed him forward forcing his cock into Todd's ass with one swift motion. She said, "Come on, get moving. This isn't a quilting bee."

Despite the fact that he was penetrated before by strapon cocks, Todd gasped as the first real cock entered his ass. He raised up high at first, then eased back down. Penelope smacked Reggie's ass a few times and said, "Faster, harder. There you go. Tiffany, how are you doing?"

Todd said, "Unh, unh. OK, I guess, Miss Penelope. Ooh. Maybe a bit more lube if you please, Reggie."

Reggie pulled out his cock and squirted more lube on the tip and then shoved it back into Todd's asshole. "How's that, pretty lady?"

"Unh, much better. Thanks. Oh."

After a few minutes Reggie started to hit a rhythm, slowly pushing his cock in deeply and then pulling it out at a faster pace. Penelope stroked Todd's head for a while and then stood at the side of the bed rubbing his side then his buttocks, just above Reggie's pistoning cock. She said, "You're a beautiful girl getting fucked. Isn't that wonderful, Tiffany?" She smiled.

Todd looked back into her smiling face and said, "Yes, Miss Penelope, it's wonderful." Todd thought that the sensations were mildly enjoyable but the best part was making Penelope happy. He closed his eyes and pictured her smile.

After another few minutes, sweat was streaming down Reggie's front and Todd felt it drip onto his backside. His thrusts were getting quicker and he was groaning slightly. Penelope said, "Here it comes, Tiffany. He's taking your cherry. You're getting fucked in the ass by a guy. I'm so proud of you."

Todd said, "Thanks ... Miss ... Penelope."

Reggie let out one final groan and pushed his cocked deep into Todd's ass three more times. On the third time he stopped he spurted his load. Penelope said, "That's it, take that load."

Todd said, "Oh, my."

Reggie hunched over and leaned on Todd's back, breathing deeply. After a few moments, Penelope slapped Reggie's ass and said, "All right, you're done."

Todd pulled up his panties. Reggie stepped off the bed and put his clothes back on. Reggie said, "Well, it certainly was nice seeing you again, Tiffany." He put his hand out again, but then put it down and walked over to the bed and gave Todd a big hug. "I hope I get to see you again some time." He left the room.

Penelope said, "Tiffany, go downstairs and tell Samantha and Kelly it's Candy's turn now."

After a couple minutes Chris and Todd came into the room followed by Samantha. Kelly walked in next followed by the rest of the sorority pledges. They were chatting amongst themselves genially. They sat down on the folding chairs.

Penelope looked at one of the pledges and said, "Donna, what is that?"

Donna held up a bowl she was holding and said, "What, this? Just some popcorn." The rest of the pledges laughed. "What's so funny? I like to have popcorn at the movies and sometimes when I watch TV. I figured this was no different. She put a handful of popcorn in her mouth and passed the bowl around."

Penelope shook her head and said, "Whatever. Just make sure you give Candy here your undivided attention. Most of you were here to watch the end of the 'Oral Lessons' a couple days ago, but I think you're in for a real treat today. Today you will witness the sublime act when a girl becomes a woman. That's right, Candy will be deflowered before your very eyes." The pledges clapped and whooped uproariously. When the noise died down Penelope continued. Todd was standing to her right and she slapped his ass and said, "This one here was a bit shy and preferred to give up her maidenhead in private..."

The crowd of pledges said, "Aw."

"But we're fortunate that Candy wanted to give it up in front of all you. Isn't that nice of her?" The pledges started whooping again which drowned out Chris as he tried to explain his version of the events. "All right, Candy. Hop up on the bed and get into position. On your hands and knees. That's good." She addressed the audience. "This is not really a formal lesson, but go ahead and shout out any encouragement or suggestions."

Samantha was waiting at the door and when Penelope looked at her and nodded she opened the door and let someone into the room. Penelope said, "We gave Candy her choice of beaus and naturally she chose the most handsome one."

The pledges started clapping as the man smiled. He started taking his clothes off and left them in a pile on the floor. Todd turned to look at who had come into the room and instantly recognized the man. He had only seen him one time, but he remembered him well. His name was Rick and he was a tall black man, solidly built, who seemed to know Penelope. He met Rick at a party the very first time he dressed up as Tiffany. It was only one kiss, but the experience had returned to his thoughts several times over the previous days.

Todd scrunched his face into a frown and thought, that bitch Candy. He scanned through his memory to see if he had mentioned Rick to Candy in conversation. He couldn't think of a time, but he probably had. Or maybe Candy had seen Rick and her together at that party. And now she was scheming to steal him away for herself.

Todd sat down hard on a folding chair and crossed his arms. Rick got up onto the bed and positioned himself behind Chris. Penelope handed his something and there was some back and forth between Penelope and the pledges, but to Todd it seemed a million miles away. He thought back to the experience he went through with Reggie. Reggie was sweet and he actually didn't mind the whole thing very much at all, but to know that his first time might have been with Rick, now that would have been special. Somehow Candy had managed to hog Rick all to herself. That absolute bitch.

Penelope slapped Todd's face lightly and said, "Earth to Tiffany. The action's over here, princess. I know you're jealous that Candy is getting all the attention, but you made your choice." Todd made a pouty face and looked up. Chris was leaning so far forward that his head was lying on the bed. Rick was behind him, hands held on each hip. His dark glistening cock pumped in and out of Chris' ass. Todd scowled.

Penelope pushed down on Chris' back and said, "Arch you back more, Candy. Yes, like that. Doesn't that feel better now?"

Chris said, "Oh yes, Miss Penelope."

The popcorn bowl was being passed around by the pledges and between mouthfuls of popcorn they where alternating clapping and yelling out things like, "Pump that ass."

Penelope said to the pledges, "You better watch your boyfriends while Candy's around, girls." Rick smiled. "How is that, Candy? Do you like that big hard cock going in and out of your ass?"

Chris seemed to think about it a moment and then said frankly, "Yeah, I think I do. I think I actually do. Unh. Unh. It's not so bad once you get used to it. And after a while it starts to feel good." The pledges laughed loudly.

Penelope was taken aback and said, "Well, er, that's right. Uh, that's how it should be." Regaining her composure she said, "You go, girl. Work it." Rick pumped Chris' ass for several minutes and the room became quiet. Only some low grunts could be heard from Chris as he wiggled his rear end slightly to the left and right. He had his eyes closed and just the tip of his tongue peeked out of the corner of his mouth. First to the left. Thrust, thrust, pump. Then easing over to the right.

Penelope walked up and stroked Chris' side. Chris looked up at her and smiled. Penelope said, "I do believe that Candy has found her groove." Noise once again reigned in the room as the pledges laughed boisterously.

Todd couldn't bear it any longer. He stood up and said, "Miss Penelope, I'm not feeling well. May I be excused?"

Penelope looked annoyed and said, "Oh, all right, why don't you get some fresh air. She checked her watch. But I want you back here in fifteen minutes."

"Thank you, Miss Penelope." Todd left the room.

Penelope turned to Samantha and said, "I wonder what got her panties in a bunch." She shrugged and turned back to Chris. "Candy, don't you think you should thank your boyfriend? Tell him how much you enjoy the thorough ass reaming he's giving you?" Chris put his head down and whispered something.

Penelope put her head down and said, "What was that?" Chris whispered in her ear. Penelope slapped her hands to her face and said, "Oh my gosh, where are my manners?" She turned to the audience of pledges and said, "Candy confessed she doesn't even know the name of the man who's fucking her ass. I didn't make proper introductions. Candy, this is Rick. Rick is the guy planting his long hard dick into your delicate asshole. Rick, this is Candy. Candy is that wanton slut on her hands and knees in front of you."

Chris turned his head backwards slightly and said, "Pleased to meet you, Rick." The pledges found this especially funny and guffawed loudly. Rick smiled.

Penelope said, "For future reference, Candy. It's often customary to get the name of the guy before he gives you a savage boning. Now that you've been properly introduced, don't you think it's time to thank Rick for coming in and making you a woman? How much you enjoy getting fucked."

Chris said, "Yes, I do like getting fucked in the ass."

Penelope said, "Don't tell me, tell him."

Chris turned his head halfway to the left and looked back and said, "Rick, thank you very much for fucking me. You're hot ... and you make me feel good. I love it when you push your cock all the way in." He turned to Penelope and said, "I'm not sure what else to say."

Penelope patted Chris' head and said, "That's fine, honey. You did well."

After a few more minutes Rick got into his own groove. He was pumping away and the pledges were chanting in time with his thrusts, "Stroke. Stroke. Stroke."

Finally, Rick pumped a last few times and with a slight groan came in Chris' ass. Chris worked his ass back and forth on the cock a few times then wiggled his ass and said, "Mmm."

Penelope looked down at the bed and said, "It looks like you leaked a little there, Candy."

Chris blushed and said, "Sorry, Miss Penelope. It felt so good." The pledges laughed. Penelope smiled.

Rick got up, got dressed, and left the room. A couple minutes later Todd returned. Penelope said, "Feeling better, are we, Tiffany?"

Todd looked around the room and said, "Yes, Miss Penelope, I feel a little better."

Penelope addressed the pledges, "All right, that's the end of the show for now." Everyone started to get up to leave. "You girls relax for a few hours. We're getting ready for the last event tonight."

Chris said, "Last event?"

"Yes, the last event of the contest of course." Penelope held the door open as the pledges, including Samantha and Kelly left the room. As she went through the door she said, "You know Tiffany, you could learn a few things from Candy."

Chris smiled dumbly. Todd said, "What are you smiling at, you slut."

Chris said, "What's wrong with you? Why are you so mad."

Todd said, "Never mind, just stay out of my way."

**********

Three hours later Chris and Todd sat together in front of a large desk in what Todd thought of as Penelope's office. Samantha had fetched them there from their room, but she left them alone in the room together. It was eerily similar to the first day they met, except that now there were only two of them. Chris and Todd looked at each other quizzically. They both were wearing T-shirts and jeans.

Chris tugged at his color and said, "This is weird. I wonder why they wanted us to wear boy clothes?"

Todd was silent.

Chris said, "Come on, say something already." Todd stared straight ahead. "It just occurred to me what Jasmine said about pictures." Todd continued to ignore him.

After a few minutes the door opened and Penelope walked through. The last time they had seen her in this office she was dressed in a business-like manner, but now she was more casually dressed in jeans with a white T-shirt. She stood beside them and said, "How are you two doing?"

Chris said, "Fine, Miss Penelope."

Todd shrugged.

"No adverse effects from your activities earlier? That's good. I hope you rested up. I'm going to take you through the rules for the last event. It's going to be fairly elaborate."

Chris said, "Is that why we got dressed up in boy clothes, Miss Penelope?"

Penelope smiled and said, "Yes, that's it. That's how you're going to start out. Do you think you can handle that or is it too much of a stretch?" She squinted her eyes at Chris and said, "You did put on what Samantha and Kelly laid out for you, didn't you?"

Chris smiled nervously and said, "Yes. For the most part. I didn't think it would hurt if I wore my panties, though. That's not a big deal, is it?"

Penelope smiled and fluffed Chris' hair. She walked behind the desk and sat down. "No, I think I can overlook that. Tiffany, I can see your dour mood hasn't lifted. Hmm, let's think. I don't know what it is but when I look at you two I don't get a masculine vibe at all. Are you sure you washed all your make-up off?" Chris and Todd nodded. "Well, let's see what we can do to get the testosterone pumping. I want you looking like two normal guys when we start things off."

She stood up and paced around the room for a few moments. She put her hand to her chin and said, "Hmm, why don't we have a little arm wrestling competition? Candy, you come around this side of the desk and Tiffany, you stay there. Excellent."

There was a light knock at the door and Samantha walked in. Penelope asked, "Is everything set?"

Samantha nodded in response. She said, "What about here?"

Penelope said, "Oh, we're nearly ready here. I'm going to take a few minutes to go over the rules, but right now I wanted get them into a more masculine frame of mind. They're going to arm wrestle. Come on, you two, let's get it started."

Samantha said, "Cool. Who do you think is going to win?" Chris and Todd started arm wrestling.

Penelope said, "It's hard to say. Candy has a few inches on Tiffany, Candy, but is also a little thinner. This might be close."

For several minutes Chris and Todd struggled with each other. Finally, Chris pressed Todd's wrist to the desk and squealed in delight that he had won. He raised up both arms over his head and said, "Yes!"

Penelope said, "Good job, Candy. Do you think you could beat me?"

Chris said, "I don't know, Miss Penelope. I don't think I want to try."

"Oh, come on now. Let's make a little bet. I'll bet you five dollars that I can beat you."

Chris looked at her for a moment, then put his elbow down on the desk and said, "You're on."

Todd showed interest in the competition and in less than a minute Chris had Penelope's wrist pinned down against the desk. Chris said, "I won. I can't believe I won."

Penelope stood up and pulled out a five dollar bill from her pocket and handed it over to Chris. She said, "Here you go. You won this fair and square. I should have known not to bet against you." She looked at Todd and said, "How about you, sour puss? You want to give it a try?"

Todd said, "I don't think so, Miss Penelope. I'm sure you'll win."

"You can at least give it a try. Same wager, five dollars." She waved her hand resting her elbow on the desk.

Chris got up and said, "Come on, Tiffany, give it a try. I know you can do it."

Todd sat down and said, "Oh, all right." He clasped hands with Penelope and started to arm wrestle. He struggled longer than Chris had done, but he too managed to pin Penelope's wrist to the desk.

Penelope rubbed her bicep and said, "Hooey, that was quite a work out. She stood up and pulled another five dollar bill out of pocket and presented it to Todd. She said, "I didn't think you'd do it, but you win the bet, too."

She walked around behind her desk and Chris got up. She sat behind the desk and Chris took his place in front of the desk. Penelope said, "You fellas certainly got the better of me. I should have known not to bet against you." Chris and Todd looked at each other and smiled. Then Todd suddenly stopped and looked away. Penelope looked at Samantha for an instant, then back at Chris and Todd. "Now, are you feeling pumped up?" Chris and Todd nodded. Penelope picked up a clipboard from the desk and said, "Great, now pay careful attention and I'll go over the rules."

**********

An hour later Penelope stood in the large basement of the sorority house. Normally used for storage and occasionally for large parties, the area was now cleared out except for some furniture in the middle of the room and was ringed by fifty folding chairs. Most were occupied and people were chatting and music played in the background. The lights were slightly dimmed and Penelope stood next to Samantha. Behind them, a bright neon sign pulsed.

Samantha squinted her eyes at the sign and said, "I don't get it."

Penelope said, "Take a few steps back."

Samantha stepped away from the sign and laughed suddenly. She said, "Oh, I see now." The neon tubes made the figure of a man. It blinked and a few different tubes lighted up combined with most of the previous tubes in such a way that the figure which was clearly a man became a woman in the next blink. Samantha said, "Geez, where did you ever find that?"

Penelope said, "Find? What do you mean find? I commissioned this baby. Cost me a pretty penny, too."

Samantha said, "Well, I'm sure you'll find some may to make back your money."

Penelope surveyed the room and said, "You did well, Sam. I'll be proud to count you as a sister tomorrow."