Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Romantic, CrossDressing, First, Exhibitionism, Slow, School, .

Desc: Sex Story: Chapter 1 - We're back at Syracuse University and the Yankees and Red Sox are in the AL Championship Series again. Mitch and Callie have new roommates. Freddie is a Sox fan and Vinnie likes the Yanks. Will there be a bet? Of course!

I was surprised, actually--at how much I enjoyed my freshman year at college, right from the start. I was a little scared before I went, but it turned out to be a blast from almost the first day.

I'm Freddie, by the way, Freddie Montclair. Yes, I'm a girl. Freddie is short for Frederica which is some old great-aunt's name I got saddled with. Dad was probably looking to be written into somebody's will. I love my parents dearly, make no mistake about it, and my upbringing was satisfying and very loving--but my parents are a wee bit money-obsessed. Which baffles me, because we have more than enough.

Anyway, somehow I got stuck with the name Frederica. I've learned to deal with it. Not always easily, mind you. Every time I got mad at my father I threatened to change my name to Susan. Evidently there are no rich Great Aunt Susans in the family, so that wasn't going to fly. I learned to look on the bright side of it--at least there were no other Freddies in all my years of school. No other female ones, anyway. My best friend Caitlin had it worse--when you called her name seven girls came running. I'd rather be Freddie.

I'm babbling again. I do that.

Anyway, I grew up as a girl Freddie in a very ritzy town: Dover, Massachusetts. The place just reeked of money. Don't get me wrong, I'm not going to give you any poor little rich girl whines. There are bad things about growing up rich but I know damn well it beats the alternative.

Anyhow, one of the less pleasant things about growing up the only child of rich and doting parents is expectations. Now, I'd done pretty well at meeting them. Until it was time to go to college.

Dad and Mom both went to Harvard. So, of course, I was going to go to Harvard. It didn't matter that my grades and test scores weren't quite Ivy League material. They were good, but not that good. That didn't matter, however--Dad and Mom both went there. If that wasn't enough, Dad could send in a hefty contribution. We all know how legacy admissions at prestigious colleges go. Come on--you think George W. Bush would've gotten into Yale if his name were George W. Klingenhopfer? Not hardly.

So, I had my pre-printed ticket to Harvard. Only problem was, I didn't want it. There were a number of reasons. The first is, I'll be honest--I was sick of snobs. In Dover, there are a number of them. Dover-Sherborn High School is Snob Central. If I'm honest, I admit that my parents probably qualify. Heck, I might even qualify in my weaker moments.

Now, I know not everyone at Harvard is a snob. However, the non-snobs at Harvard are generally more prevalent among those who actually got in on merit. And that was the other reason. Look, like I said, having a rich daddy beats hell out of the alternative. However, I'd honestly rather not coast on his coattails my whole life. My grades were good--maybe not Harvard-good, but good. I knew I could get into a good school on my own, not because I was Child of Wealthy Alumni.

I applied to quite a few, actually. I picked Syracuse. It was a good school, and far enough away that my overprotective parents couldn't be breathing down my neck. They weren't happy, of course--because I wasn't close, and because Syracuse wasn't Harvard. For once I stuck to my guns. Syracuse was where I headed.

And, as I said, I loved it, right from the first day. It was a big campus--I liked that. Look, I'd been very sheltered. It was almost an overdose of freedom. It could have been a disaster, actually, except I got lucky. I got the world's greatest roommate--Callie Durban, a junior.

Callie was great. She watched out for me without actually watching out for me, if you know what I mean--she wasn't overbearing. She was just helpful. She gave me good tips about navigating the pitfalls of your freshman year at a big university. She helped me after my first big hangover. And she wasn't at all put out about having a lowly freshman as a roommate, which surprised me. Especially when she told me she didn't even have a roommate last year. "She never showed up," Callie told me. "But I didn't pay for a single so I knew I wouldn't get one this year."

So, she was cool about having a roommate. I'm sure part of that was that she really had her life together. She was a good student, had a nice circle of friends, was able to balance everything, and had a really cool boyfriend, Mitch.

And, as the semester got going, I learned to appreciate Mitch more and more. You see, there was one area where my roommate and I did not get along. Baseball.

We both loved it, which was cool--there were girls that were baseball freaks like me, but they were in the minority and it was good to be rooming with one.

Unfortunately, Callie was the worst type of baseball fan--she liked the Yankees. UGH!

Hey, Dover was only 15 miles southwest of Boston. So I was, of course, a Red Sox fan. A Red Sox fan and a Yankees fan are like oil and water. When I found out that Callie liked the Yankees, I said, "Uh-oh. You think we should find new roommates?"

"Nah," she laughed. "If I can go out with a damn Red Sox fan, I can room with one." Mitch, who was there, shot me a smile.

"You? Red Sox Nation?" I asked.

"You betcha. I'm from Medford."

"Cool! I'll have someone to commiserate with! But how the hell can you two go out without killing one another?"

They both laughed. "We just realize from the start that we're going to fight every time the Yankees play the Sox," Callie said.

"In fact, it was last year's ALCS that brought us together," Mitch said.

"Long story, but, yeah, it pretty much was," Callie agreed.

"And now I'm in the same boat as you are, rooming with a Yankees fan," Mitch pointed out.

Oh yeah--Vinnie.

By the time October rolled around, I'd been at college a little more than a month. I'd decided a few things. One was that I loved Callie, really liked Mitch--and didn't like Vinnie at all.

Vinnie Morello. Vinnie from Brooklyn. He was also a freshman, and was Mitch's new roommate this year. And, boy, did he hit every bad stereotype I ever had of Yankees fans. Callie didn't but Vinnie did.

Look. The Red Sox never actually win, so we have to get out our frustration in other ways. And Bostonians are provincial as hell, anyway. So, the Yankees might win all the pennants, but their fans are cretins, is the line of thinking. One joke goes like this: why do Yankees fans chant "1918!"? The Yankees fan will tell you it's to make fun of Red Sox fans, the last World Series and all, but we Sox fans know better--it's because 19 is as far as a Yankees fan can count, then they have to go backwards.

You grow up in Boston, you hear that stuff all the time.

Well, my first impression was that Vinnie fit the bill. A big, dumb, hairy Italian goon from Brooklyn. He made you want to make ape noises. He made you want to ask where his Camaro was. He made you want to throw up. It was loathing at first sight--and that was before I even knew he was a Yankees fan.

Vinnie from Brooklyn. What a cliche.

Of course, he thought I was, too. He immediately branded me a snob. I am NOT a snob. Just because I can use dining utensils properly and don't have to comb my back hair doesn't make me a snob.

It doesn't!

Well, maybe towards him I was. But that's because he was a dumb Noo Yorker Yankee Fan.

The Yankees won the division, the Sox won the Wild Card. Just like last year. And the Yankees defeated the Twins and the Sox defeated the West Division Champions--this year the Angels--just like last year.

We were hanging out on Saturday, October 9th, after the Yankees eliminated the Twins. The Sox had taken care of business on Friday.

"Here we go again," Mitch said with a laugh.

"Yep," Callie agreed. "And besides each other, now we got these roommates to argue with. This ought to be interesting."

"Yeah, for the four games the series lasts," Vinnie butt in.

"You must be predicting a Red Sox sweep, then, since game one is in the bag," I said. "No way the Yankees beat Schilling in a playoff game."

"She's right," Mitch interjected.

"The Yankees are a far superior team," Vinnie maintained. "Who won the division?"

"Who won the season series?" I countered.

"Ah, that doesn't matter."

"Sure it does. Let's face it, you're scared to death, because for the first time ever the Red Sox have better starting pitching."

"The Yankees have a better lineup," Vinnie argued.

"Really?" I said sweetly. "Funny, the Red Sox scored more runs. Had a better batting average, a better on base percentage, a better slugging percentage. Across the board--doubles, hits, batting average--the Red Sox were better. The only thing the Yankees were better at is home runs."

"And winning. Hey, winning can be a talent, just like anything else."

"True," I said, impressed--that was almost profound for Vinnie. "But this isn't the Paul O'Neill, Scott Brosius, Andy Pettite Yankees. Only guys left from those teams are Jeter, Rivera and Bernie Williams, who isn't what he was."

"Yankees are still gonna win," Vinnie insisted.

"Hey, you guys should make a bet," Mitch put in. Callie giggled at this, making me wonder.

"Us guys? What about you two?" I asked.

"Nah, we did ours last year," Callie said with a laugh. Obviously there was a story in there. Hopefully, I'd hear it some day. "You two should go for it."

"I'm game," Vinnie said. "How much? And keep it out of the millions, Princess, some of us don't have access to Daddy's platinum card."

Princess?!? What an ass! "I'll have you know..." I started, indignantly.

"Whoa!" Callie interjected. "You guys shouldn't bet money. What fun is that? We didn't. You have to make the other person do something. That's more fun."

Oh, there was definitely a story in there! I'd have to press Callie. "Something to do, huh?" I said.

"OK, I'm still game," Vinnie said. "We just have to think of something. Loser buys the winner dinner at a restaurant or something?"

Yeah, like I was going to walk into a restaurant with Vinnie the Goon! "Maybe, let me think," I said.

"It should be more evil than that," Mitch said with a wicked grin, egging us on. Callie and Mitch were having great fun with this.

That's when I got an idea. It was evil. Very evil. But I looked at Vinnie sitting there glaring at me, oozing misplaced testosterone, and that's when the idea popped into my head.

"Here's the deal," I said. "We watch every game together, just the two of us. It's a best of seven series, takes four to win, right?" Vinnie nodded. "Well, after every game the Red Sox win, you have to watch the next game with me wearing an article of women's clothing. If the Sox win, which makes four, you'll be fully dressed for the first game of the series. First win is bra, second panties, third pantyhose, and fourth is a dress. Maybe even a little lipstick for that one," I giggled.

"Oooh, that's nice and nasty!" Mitch said approvingly.

"You have GOT to be KIDDING!" Vinnie roared. "You expect me to watch the game with you in a bra and panties? Or a dress? No way."

"Oh-oh," I said, "I guess poor Vinnie isn't very secure in his masculinity, is he?" I teased.

"I am so! Which is why I don't want to wear girls' clothes!"

"Well, that's my bet." I paused for a minute. "Chicken."

"Well, what do I get if I win?" he said.

"Think of something."

He gazed at his navel for a few minutes, then I saw something shift in that Neanderthal brain of his. And he came up looking very satisfied with himself. Uh-oh.

"Fine, if that's the way you want to play it, I've got it. We can stick right with the clothes theme." Double uh-oh. "For every game the Yankees win, you watch the next game with me without an article of clothing. Socks and shoes don't count. Since I don't see you in dresses and pantyhose much, we'll do the four as top, bottom, bra, and panties."

Definitely uh-oh. "So, if the Yankees win game one, I'll have to take my top off for game one?"


"And if the Yankees win the series, I have to watch the first game of the World Series with you completely stark naked?"


"You have GOT to be KIDDING!" I thundered.

"Didn't I just say that?" Vinnie said, bemused.

"You just want to see me naked, you pervert!"

"I'm a pervert? Who's playing gender-bending games here?" Vinnie laughed.

"No way. Think of something else," I said.

"Nope. That's the bet, or the bet's off. I'll agree to take the risk of wearing a dress. And knowing you, if it ends up happening it won't end up secret. You'll probably sell tickets."

"You think I'd do that?"

"In a heartbeat," he said. I could've tried to be offended but he was probably right! "So, that's what I'm risking. I want a good payoff."

"Yeah, and I end up naked in your room and you're selling tickets. Or passing out binoculars along the way."

Suddenly, he looked very serious. "No way. I would NEVER do that. I understand that making me dress up in a bra and frock is prime teasing material. Getting naked is not, or shouldn't be. If you lost this bet, you would come to my room completely clothed, I would lock the door and pull down the shades, and then you'd get undressed. Nobody else would see or know. I'd never do that to you. I promise." Somehow, I believed him. Don't ask me why.

"I appreciate that, but I still think it's too much."

He dropped the serious look on his face and went back to his usual stupid smirk. "What's the matter, Princess? Chicken?"

"Don't call me that!"

"It's what you are, Princess. Royalty, so far above us mere mortals, certainly far above disrobing anywhere near the peasants. But you're a chicken, Princess. And you obviously think the Red Sox are going to end up losers again."

"Fine, dammit! You're on!!!" The words were out before I could stop them.

"Good," he grinned. Mitch and Callie were giggling in the background. "I'll see you Tuesday evening, for game one. You get to be fully clothed for that one."

Oh, shit. What had I done?

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Story tagged with:
Ma/Fa / Romantic / CrossDressing / First / Exhibitionism / Slow / School /