Part 6

Laying in bed, Todd heard someone rustling from the other side of the room. Not moving himself, he whispered out the side of his mouth. "Candy, do you hear something?"

Chris woke up and said, "What?"

"Shh. I think there's someone in our room."

Both Chris and Todd slowly rose up and saw a figure standing at their dresser at the other side of their room with his back to them.

Chris said, "What's a man doing in our room?"

The man was stealthily and methodically going over the items on their shared dresser, all their make-up and the wigs they used to turn themselves into their feminine alter egos Candy and Tiffany. This was the fifth morning since they started participating in the "Best Girl" competition. The contest was being run by Penelope from the Alpha Phi sorority and both Chris and Todd had hopes to win a wild card bid to become a member of the Beta Phi fraternity. There were originally three contestants, but Jack (who became Jasmine) was unceremoniously kicked out of the house the previous day.

Chris and Todd got out of bed quietly and crept over to the shadowy figure. Chris was dressed a brand new red satin babydoll with a matching red thong. Todd was wearing a blue lace merrywidow with matching thong. Todd fell to the floor and hugged the man's legs together at the ankles. He struggled to force the man to the ground. Chris stepped in and shoved the man at shoulder level. With Todd holding his ankles, the man lost his balance and toppled over.

Todd stood up and quickly said, "What are you doing in our room? You shouldn't be in here. We're barely dressed. Are you a peeping tom? Or some kind of pervert?" He pulled his foot back and kicked the man in the testicles.

The man said, "Oof!" and crawled into the fetal position.

Chris said, "Maybe he's a panty raider. Is that it? Are you trying to steal our panties?" He tried to kick the man in the crotch as Chris had done, but the man was using his legs to protect himself.

Todd was aghast. He said, "Our panties! Oh, you terrible man." The man was lying on his back and Todd sat down on his chest so that when leaning forward he could force the man's legs open. With a clear target, Chris finally connected with his foot.

The man started to yell, but Todd said, "Quiet, you." and scooted backwards so that his ass covered the man's face. He grinded down, smothering the man's face completely.

The man said, "Mmph, mmph," but after a few tries finally managed to push Todd off of him. They tangled on the floor for a while longer and the man got the upper hand. He sat up straddling Todd's face and said, "Will you two hold on just a minute."

Chris grabbed something from the dresser and started to hit the man with it. The man fended Chris off with his hands. He said, "Stop it. Stop hitting me." He lunged for the object and managed to take hold of it. It was a large black silicone dildo. He laughed and said, "I should have known you couldn't keep your hands off a dick for long, Candy."

Chris squinted and looked at the man and said, "Jasmine, is that you? Is it really you?"

Jack got up off of Todd and they both stood up. Jack said, "Well, just Jack now I guess."

Todd said, "What are you doing? What happened to you yesterday? What time is it?"

Jack said, "Shh, keep your voices down. Hopefully that little scuffle won't bring anyone up here, either. I'm not supposed to be here but I came back for a couple things - my wallet being the main one." He started looking through some drawers as Chris and Todd put on their wigs and tried to make themselves halfway presentable.

Todd said, "Why would that be in here? I haven't seen any of our old things whatsoever."

Jack shrugged and said, "Yeah, I guess not. It was a long shot, really. I can't risk spending much time in any other part of the house, but I figured I could sneak in here at least." He sighed and went and sat down on the bed.

Chris smiled and said, "Look at you. I barely recognize you. You're kind of cute as a guy." He sat down closely next to Jack on the bed and took hold of his hand. "It's nice to see you."

Todd said, "Candy, it was only one day."

Chris said, "Well, a day can be a long time."

Jack said, "You're telling me. You won't believe the day I had yesterday. Ugh. I'm not even going to go into details."

Chris said, "You've got to tell us something. Inquiring minds want to know."

"Is that so? Well, what happened with you? I didn't expect you two to even be here. How come you didn't get kicked out like me?" A sudden thought occurred to him. He slapped Chris hard across the face and said, "You slut! You're the one who instigated the pact and as soon as I'm gone you turn around and offer up your ass to any takers. Come one, come all. That must have been your plan all along. Pretend you're squeamish about bending over and taking guys' cocks in your ass, but then once I'm gone it's open season."

Chris didn't say anything at all. He stared straight ahead for a few moments, then his face squinched up and he started to cry. He said, "How can you say such things about me? I would never do that to you. That's not how it happened at all."

Jack softened and said, "There, there, Candy. I didn't mean to make you cry. There, put your head on my shoulder. Tiffany, why don't you tell me what happened."

Todd said, "Well, we didn't outright refuse. We didn't get a chance to. Once Penelope found out about the pact she went ballistic. First we had to write lines on the board."

"Big deal."

Chris had finished his sobbing and said, "It's worse that it sounds. And Kelly was hitting us with that pointer-thing the whole time."

Todd said, "We went back to the PleasureDome, sucking cocks this time."

Jack said, "But you've even been there before and don't even try to tell me cocksucking is something new to you. So far it doesn't sound so bad."

Chris said, "Oh, but this was different. Miss Penelope left for a minute and the men turned into absolute animals."

"So they rescued you? That can't even count as a punishment. What else?"

Todd thought for a minute and said, "Hmm, then we gave foot massages for most of the afternoon, to try to make back some of the money Miss Penelope lost when we misbehaved."

Jack said, "Foot massages? Come on, that's a cakewalk."

Chris said, "You wouldn't say that if you had to do it. Foot after foot after foot. I got almost all the guys, too." Chris' panties started to tent.

Jack said, "I can see what a hardship it must have been. Stop right there, I don't want to hear any more. I knew I made a mistake and this just proves it more. Darn my rotten luck. I didn't even care that much about getting butt-fucked, not like you, Candy. I was just going along and I paid the price."

Chris said, "Price? What price?"

"I'll tell you. First of all, it wasn't a walk in the park getting from here back to my dorm room dressed as I was in my schoolgirl uniform. No money. I think I would have been better of if I had just stripped down nude. But I don't want to go into that. Let's just skip forward to when I finally got into my dorm room. Since I hadn't checked it for a few days naturally I had a lot of e-mail. However, it was the last few that caught my attention. The first looked like the usual spam except that the subject caught my eye. It was something like 'the best girl you'll ever see' and the from address was my own campus e-mail address. The e-mail was set up like it was coming from someone promoting an adult web site. I don't remember it exactly, but it said something about free trial access and the internet's brand new 'tv harlot'. It had my full name and what startled me even more was a picture of me in drag as Jasmine." Chris and Todd gasped.

Jack said, "It looked like that day we went shopping. I checked out the site and there were more pictures there. I checked the e-mail again and saw that it was sent to a lot of people. The boss at my off-campus job. My resident assistant. The school administration. Up and down the line. That's when I looked and saw that the following e-mails were from those same people, responses to that original message. I lost my job. Got kicked out of the dorms. And I'm on suspension from school. My life's a total wreck. I thought maybe I'd find something back here, like my driver's license or credit cards. Even some cash would help."

Chris said, "Who do you think sent the message? How did they get pictures of you?"

Todd said, "It doesn't make any sense to me. How could all that stuff happen in one day? What were the other pictures of? Were there any pictures of us?"

Chris said, "Maybe Miss Penelope can help you out."

Jack gave Chris a severe look and said, "Candy, who do you think is behind it all? Anyway, I can't stay here and chat. I have to get going before someone comes in."

Todd said, "Wait a minute. Can't you fill us in a bit more?" He reached out and grabbed Jack's wrist.

Jack stood up and pulled his hand away. He said, "No, I have to leave. I'd like to help you girls out, but I have problems of my own. I wish I could take it back. I don't care what would have happened it would have been preferable to what I went through." He looked down at Chris and Todd. "I wasn't expecting to see you two here all Holly Golightly, without a care in the world. I must say that I'm hurt with the way things turned out and the way you two schemed behind my back to get my out of the contest. Girls should stick together." He turned around abruptly and walked to the door. He opened it and carefully peered to the right and left, then exited the room.

Chris said, "Jasmine, don't go. Don't be like that." He stepped out into the corridor but Jack had already gone. Chris rushed to the window.

Todd joined Chris at the window and they both looked down as Jack went through the door and walked down to the sidewalk. They both turned away from the window and sighed.

Todd said, "That's a lot to take in."

Chris said, "Yeah. I'm not sure what to think."

Todd said, "Well, does it make you reconsider your position? Do you think you'd be willing to allow... Do you think you'd submit to... Uh, do you..."

"Oh come on, Tiffany, just say it. Do we want to let guys fuck us in the ass? I don't know, I just don't know. If you asked me a week ago I would have laughed. Even a couple days ago, it would have been an easy answer, but now I'm not so sure. After yesterday and this thing with Jasmine I wonder if it would just be easier to go through with it."

Todd said, "I was thinking that myself."

There was a knock at the door and Chris and Todd rushed to put on their wigs and get themselves into a semblance of order. A dab of lipstick for Todd and a swipe of blush for Chris. They each shrugged a fluffy robe over their nighties and sat down on the coach as the door opened.

Penelope walked into the room hesitantly dressed in a short red satin robe and said, "Girls, is it OK if I come in and talk to you for a minute?" Chris and Todd nodded and Penelope wedged in between them on the coach. She put each of her hands on one of their knees. She said, "I just wanted to check up on you and see how things stand. As far as I'm concerned today is a new day and nothing need be carried over from any past wrongdoing. I think if you're up front and honest with me then we can discuss things and hopefully I can alleviate any concerns you have."

Chris said, "Miss Penelope, what are you going to make us do today?"

Penelope said, "Candy, I'm not going to make you do anything. If I get your consent, I'm going to see if I can salvage some of the activities I had planned for yesterday."

Chris said, "And that was?"

Penelope said, "Come on, Candy, you know exactly what I had planned. You were going to get a lesson in anal intercourse. With the way you're carrying on it's a subject you sorely need instruction in."

Chris said, "But why do we have to do that?"

"Look, this might be a silly contest to you but I take it very seriously. Part of your education as a girl requires intercourse with a man. Doesn't that make sense to you? Isn't that logical?" Chris nodded. "I would be short changing you if I didn't find some way you could experience it. Now, this isn't a knock on you girls, but as much as you might wish otherwise you do not have the proper equipment. Luckily, you have the next best thing to a pussy. You will be introduced to anal intercourse and learn to satisfy a man with your ass."

Todd said, "But Miss Penelope, won't that turn us into homosexuals?"

Chris said, "Yeah, that's my point, too. I don't want to be gay."

Penelope said, "Girls, girls. Who said anything about being gay? You enjoy dressing like girls, does that make you gay? Of course not. You like it because it feels good and you see that it pleases me. You want to make me happy, don't you?"

Both Todd and Chris said, "Yes, Miss Penelope."

"And by now you both have given your fair share of blowjobs. Did that make you gay? Of course not. Again, you did that because it felt good and you wanted to please me." Chris and Todd didn't seem convinced. "Look, you're doing all these things as girls. How can it possibly be construed that girls having sex with boys is gay? That's utterly ridiculous. As long as you're dressed as girls and thinking of yourselves as girls it's perfectly normal. I'm sure if you look at yourself deep down you already know that." Chris and Todd sat on the couch silently for a few moments.

Penelope stood up and said, "I think I see where the problem was. Obviously the physical part of it wasn't a problem because you had no problem getting fucked with our strapons on either occasion. But there was some kind of strange mental block you were having." She opened her robe. Underneath it, she was dressed in a bra and panties that matched the robe. "Look at me for a minute." Chris and Todd gazed longingly over her body. "Are you attracted to me?" Both Chris and Todd nodded their heads vigorously. "All right, I don't want to hear any more of your fervent claims that you're homosexuals." She left her robe open and Chris and Todd were still staring intently at her body. "Now, do I have your consent to continue today's activities?" Chris and Todd nodded. "Good." Penelope closed her robe. She said, "Is there anything else?"

Todd said, "Miss Penelope, it seemed like there was an audience set for yesterday's lesson? Is it going to be the same way today?"

Penelope said, "Oh, Tiffany, you bashful thing. Are you worried about people watching you for your first time?" Todd looked down at his feet and nodded his head. "Hmm, let me think. I'm feeling generous so I'll give you a choice. For your first time you can either choose to have no audience, just to be alone in the room with me and your man, or you can choose which man gets to do the deed."

Chris half-raised his hand and said, "Miss Penelope, is it going to be those same hot models as yesterday?"

Penelope frowned and said, "No, Candy, I wasn't going to risk any more money on you." Chris looked sheepish. "I've got a few volunteers to help us out. Now what's your choice?"

Todd said, "I'd prefer to be alone with you, Miss Penelope."

"All right, and what about you, Candy?"

Chris thought for a minute and said, "Well, I think I'd rather choose who does it. Any of those models would have been fine, but if it's just regular guys, well, I don't want to end up doing it with some troll."

"Oh, Candy, I wouldn't do that to you, but you make a lot of sense. A girl's first time should be special. I'll leave you now to get ready. I'm going to send Samantha and Kelly in and they're going to make sure you get ready properly. Come on, cheer up. Don't you know this is the last day of the contest? Tomorrow's the day that pledges become sorority sisters or fraternity brothers. It's a time for celebration."

Chris and Todd turned and looked at each other while Penelope left the room. Chris said, "The last day, imagine that."

Todd counted on his fingers. He said, "Six days. Seems longer. I guess it had to stop at some point." He looked around the room. "It's going to be weird leaving this house."

Chris said, "Yeah." Inwardly he was thinking how great it would be to win the contest and from the next day onward to spend his time at the Beta Phi house arm in arm with his fraternity brothers.

Two hours later Chris and Todd waited in their room thoroughly cleansed and prepped for their new lesson. They were wearing the brand new school uniforms that had been laid out for them. A variation of the previous uniform, these had cream-colored stockings with scallop lace at the top and matching garters where the old one had long gray wool socks. The skirt was pleated like the old one, but was a deeper gray and slightly shorter. A cream-colored lace bra replaced the plain white one. The white shirt had a softer feel and was fitted whereas the old was starchy. Their wigs were new, too, Todd noticed. His was maybe a half-inch longer than the old one although similarly styled. He chuckled to himself. Candy didn't even seem to notice. He wondered where they had put the old ones and hoped that they didn't get thrown out. Maybe he'd ask Miss Penelope about it later. He also laughed inwardly when he thought about his shirt. Initially he saw that his shirt was missing the last button and had a very pale stain at the bottom hem in the back. He distracted Candy briefly by pointing out the window at a bird and switched the shirts and she was none the wiser. Candy was sweet, but dumb as a post.

The whiteboard was set up in the room and written on it was, "Anal 101: A practical approach." Todd looked at the words and swallowed hard. Chris followed his gaze and swallowed, too. Both Chris' and Todd's knees were knocking. Two rows of folding chairs were set up against the wall, currently empty.

Penelope walked in followed closely by Samantha and Kelly. She looked over Chris and Todd and shook her head. She said to Samantha, "Did you do that?"

Samantha looked at Todd and then said, "What?" She peered closer at his crotch and said, "Sorry about that. They must have put on their gaffes when we weren't looking." She squatted down in front of Todd and pulled down his panties. Then she untied and undid the device that held his penis and testicles neatly flattened and out of plain view. Kelly squatted down in front of Chris and did the same.

Penelope reached downed and gave Todd's genitals a few whacks, then did the same to Chris. "You can't really hide that when you're bent over getting your asses reamed for crying out loud. Pull up your panties already." Chris and Todd did so. She turned to Samantha and Kelly and said, "Go ahead and take Candy downstairs and send the first, uh, instructor's aide up."

Samantha and Kelly left with Chris and Todd was left alone with Penelope. She said, "Your new uniform looks great, Tiffany."

Todd blushed and said, "Thank you, Miss Penelope."

Penelope said, "I hope you're not too anxious about this, Tiffany. It's very natural. Don't you want to do something nice for me?"

"Yes, Miss Penelope."

"And admit it, don't you like dressing up? Especially when you know that it pleases me to see you this way?"

"Yes, Miss Penelope."

"All right then, this is just another step. Trust me that when it's over you'll enjoy it every bit as much as you enjoy crossdressing and giving blowjobs."

"But Miss Penelope, I didn't say..."

Penelope put her hand over Todd's mouth and said, "Hush, Tiffany. We're having a moment here."

The door opened and a guy walked through the door. Todd recognized him at once. Reggie. He had given Reggie a handjob and a blowjob on separate excursions to a nearby adult video store.

Reggie stuck out his hand towards Penelope and said, "Hi, I'm Reggie. Pleased to meet you. Those girls downstairs told me to come up here." Penelope looked down disdainfully at his outstretched hand and he pushed it over in front of Todd. He said, "Oh, that won't do," and leaned over and gave Todd a hug. "How are you doing, Tiffany? It's nice to see you again."

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?"