Joining a Sorority Pt. 01

Jeremy and his best friend Andrew were always making bets with each other. It started in elementary school and has continued all the way to their college years. All of the bets have been getting increasingly more interesting as the years wear on, especially with the kind of money that Andrew is able to throw into these bets since his grandfather died and left him a significant amount of cash. The most recent bet almost wasn't worth it to Jeremy; at least not until he heard how much cash was being offered.

"So you're telling me that you will give me $2000 dollars if I can join a sorority? That's crazy!" Jeremy exclaimed.

"Dude, how long have we been friends? When have I ever given you a bet that I didn't think you could actually achieve? I reckon you're a shoe in for this one!" Andrew replied.

"You're forgetting the one little problem: I'm not a girl!" cried Jeremy.

"Surely that wouldn't stop 'Always-Gets-It-Done Jeremy'? I've never seen you back out of a bet before in my life!"

"Well it's different this time! This is something I could never do!" said Jeremy, concluding his argument. He knew his friend was right, though. He could achieve this bet. He was 22, five foot 8 and had a fairly slight build with long blonde hair. If it weren't for the severely masculine clothes that he wore he could easily be mistaken for a girl. This ate at him for a few weeks. Andrew didn't press the issue.

A few weeks later in the middle of their daily Xbox game, Jeremy suddenly piped up:

"That bet still on?"

"What bet is that?" Andrew replied.

"You know very well which one!" said Jeremy.

"Oh yeah," smirked Andrew, "It's still one. That's if you're not chicken enough to back out on it. And I'll make it interesting: I'll give you $2500 if you can complete it, just for the extra incentive!"

"Deal!" replied Jeremy and they shook hands; the bet was sealed.

***

That weekend, Jeremy went back to his parents' house (they were out of town) and sought his younger sister Amy's advice. She was 18 and she knew all about the bets that he and Andrew were making against each other, often helping out one or the other if needed. This time Jeremy asked a huge favour and Amy was more than happy to oblige; after all, she always wanted a big sister!

The sorority that Jeremy was to join had their annual tests which were always hush-hush, and the prospective sisters were told they must arrive in schoolgirl attire. After he arrived they got to work straight away with Amy instructing Jeremy to have a shower and shave all of the hair off his body, leaving only that which grew from the top of his head. She pointed out the moisturiser that he was going to need to calm the razor burn. She also made sure that he conditioned his long hair so that would be easier to style. Exiting the bathroom Jeremy felt the coolness of the air on his body, which he never really knew with all the hair he previously had. He moved to Amy's room where she was ready for him.

Lying on the bed was the outfit that was supposed to get Jeremy to into the sorority for the next weekend's annual 'Entry Exams' as they were known. As he was slight, her clothes would be a perfect fit. It consisted of a white lace push-up bra (including C-cup breast forms) with matching panties, a pleated plaid skirt, a skimpy blouse that was to be tied up just under the breasts, a pair of white knee high socks and a pair of black heels. A sudden pang of nervousness crept into Jeremy's mind and he found himself making excuses.

"I-I-I-I don't think I can go through with this! Everyone will know I'm not a girl! It won't work!" he cried.

"Oh yes it will!" said Amy with conviction. She was used to her brother's nervousness, "You will look perfect, especially when I'm done with you!"

With that he calmed down a bit, and Amy left the room whilst he attempted to get dressed. The panties were the easy part, he'd put on underwear before. He could feel an erection coming on, so he tucked his penis in and thought about his great grandmother, a trick that always worked. Then he attempted the bra, but had to call for Amy's help to get it on. Then he slid in the breast forms and Amy applied some makeup to the area to give the effect that the fakes were actually real. Then he put on the skirt, which stopped halfway down his thigh, and the blouse which Amy showed him how to tie up properly. Then he put on the knee socks, again knowing how they worked, and put on the heels. He stumbled on his first few steps but after being given the correct technique he was able to walk quite confidently.

Jeremy then was made to sit down so that Amy could apply some makeup to his face, and he was patient as she applied some eyeliner, mascara, lipstick and some blush. She explained that too much makeup would draw attention for being too fake; whilst just enough would complete the illusion perfectly. He saw why when he looked into the mirror. Standing in the mirror in front of him was a beautiful girl, almost a dead-ringer for Amy herself. She grabbed him around the arm and squealed.

"I wish we thought of this sooner! We can go shopping together and trade clothes and everything!" Amy gleefully exclaimed.

"Whoa, whoa, whoa! Don't get ahead of yourself! This is just a very temporary arrangement. Once I get my $2500 I won't go near another piece of girls' clothing again, unless it's to remove from said girl wearing it."

"We'll see," she said grinning, "but we need one more thing. What is your girl name going to be?"

"I dunno. What do you think?"

"I think Jemima would be perfect."

And so it was a week later, the day of the Entry Exams, that Jeremy invited Andrew over to meet Jemima. The doorbell rang and Amy answered it.

"Hey, Andrew!" she cried, "Wait here, I'll go get her!"

"Oh, okay," he replied. About a minute later the two siblings came down the stairs to a gasping Andrew, so taken aback he almost fell over.

"Jeremy! Is that really you? Damn! I knew you could pull off a girl, but not his convincingly!"

"For tonight, it's Jemima. And thank you. I'll take that money now; it's as good as got!"

"Not so fast," replied Andrew, "You still gotta pass the exams to get the money. Come on, I'll drive you over."

They arrive at the sorority house and got out of the car. Andrew walked up the Jemima and smacked a kiss on the lips. Extremely confused, Jemima froze.

"Dude, what the fuck?! Did you just kiss me?!"

"Holy fuck that was an accident! I'm too used to kissing a beautiful girl when I drop them home. Force of habit. Won't happen again!" Andrew replied.

Still somewhat mortified, Jemima walked up to the door and went inside. The front room was already filled with almost a dozen girls wanting to join the sorority, and each stared at Jemima as she entered. Before she could say anything, the head sister came down.

"Okay girls. Upstairs now! Last one up goes home!"

So the girls all rushed up, with Jemima pushing all the other girls out of the way to be there first.

"Excellent job!" cried the head sister, "What is your name?"

"Jemima"

"Well Jemima, since you're here first, you get first pick of the exam papers. Okay everyone inside!"

When the door was opened, Jemima was so surprised to see that there were a group of guys without pants on, standing in a line. When they arrived all the guys started to get hard. IT was explained that the way to enter the sorority house was to suck off one of the guys until he came and swallow the cum. The guys would judge them and the best four girls would become sorority sisters. The head sister turned to Jemima and said, "Okay, which exam paper do you pick?"

Caught in an internal monologue, Jeremy found himself rationalising his decision. It was $2500 after all, and no one would know what happened here except him. So he got practical. He found himself drawn to the guy with the biggest cock, it must have been 8 inches, and without a word knelt down in front of the guy and waited for further instructions. Once all of the girls had picked a guy, they were told to begin.

Jemima was hesitant, but the guy grabbed the back of her head and put his cock next to her mouth. Jemima started slow, gently kissing the head before licking up and down the shaft and even to the balls. Then she took his cock in her mouth and slowly began to work her way down towards the balls. After a few minutes she could feel the tickle of his pubic hair on her face. Knowing she could take his whole cock without gagging, she began to increase in speed. She knew she was doing a good job by the moans of pleasure coming from the guy.

The guy started thrusting into her face, and then with a large cry out he came in Jemima's mouth. As he pulled out Jemima swallowed his cum, remarking to herself that it wasn't the worst thing she'd ever tasted. She then continued to suck all the remaining cum off his cock as his started to go soft.

After all the girls completed their tasks, they were allowed to go to the bathroom to freshen up. So Jemima added more lipstick, fixed up her hair and went back to get the results.

As if from a scene from Masterchef, each of the guys had cards to hold up giving a score out of 10. Each guy put his card up, and it revealed that 6 of the girls got 9 out of 10. One of these girls was Jemima, who was surprised as much as she was pleased. But her smile quickly fell when she was informed of the second exam. What had she gotten herself into?