Copyright 2004 Frank Downey. All rights reserved. Any use other than personal archiving requires the permission of the author. Do not repost.

This story contains adult material. If this is illegal where you reside or if you are underage where you reside, begone.

Second thoughts? Oh, yeah, I had them almost immediately. I mean, right away. After we finalized the bet, Mitch and Vinnie left our room. I turned to Callie and moaned, "Oh, God, what have I done?"

"Hey, it could be worse," Callie grinned. "Mine last year was I had to sleep with Mitch."

"Like you don’t anyway," I smirked.

"We hadn’t at that point. We were just friends."

"Oh. What was Mitch’s?"

"He had to give our gay friend Tim a blowjob."

I broke up laughing. "Now that’s cruel and unusual punishment. The Yankees won last year, so did he?"

"No. I conceded after game five. I decided that I liked his prize better than my prize. We’ve been together ever since."

"Cool," I said. "However, I’m not so sanguine about this. I don’t even like Vinnie? And he might be the first person to ever see me naked? What have I done?"

"You don’t like Vinnie? I think he’s cool."

"I think he’s a big dumb goon."

"I think you’ve misjudged him," Callie maintained. Then she stopped. "Wait a minute. Did you just say that nobody’s ever seen you naked?"

"Unless you count, like, my mother, no."

"Freddie, are you a virgin?" she asked.

"Uh, yeah. Sheltered upbringing and all that. I love my parents, but overprotective is an understatement," I said sheepishly. "I wasn’t really allowed to date much. Getting enough privacy to do anything was pretty impossible. Making out is as far as I’ve ever gotten."

"Oh. That changes things," she said. "I didn’t realize you were such an innocent."

"That’s me," I snorted.

"Maybe you should get out of the bet," she said. "I mean, look--I really do think you can trust Vinnie. But maybe you don’t want to get naked for a guy for the first time as a bet."

"And he’ll never let me live it down if I do," I sighed. "And I have to deal with him because he’s your boyfriend’s roommate. No, I think it’ll be easier to go through with it." I gave her a wicked grin. "Besides which, the Sox are going to win anyway."

"Uh-huh," she laughed. "Dream on, little Red Sox fan." Then she got serious. "I still think you should get out of the bet. Look, I don’t think Vinnie has any idea you’re as inexperienced as you are. He’s not an asshole, he’ll understand."

"Nah. Thanks, Callie, but I agreed to the bet. I have only myself to blame. And, let’s face it, considering what he might have to do, I have to be a good sport, because he is."

"True."

----------

That next day, Sunday, I went home. I had a little problem, you see.

One thing Vinnie had asked when we finalized the bet was about clothes should he lose. It was a good question. He certainly wasn’t going to fit in any of my clothes. I’m 5’4" and about 125. He’s a good six feet and probably about 180. He’d rip one of my dresses in half, and he’d never get his big dumb goon bicep into any of my bra straps. He quickly figured that out, and asked about girls clothes that would fit him.

I had that all covered, but I had to go home to do it. My best friend Eric, you see, was a drag queen. Just about nobody knew that back home, but I did. He’d confessed a few years ago. I’d even seen him dressed. He was pretty cute, actually--except for being a pretty big ‘girl’. He was almost the same size as Vinnie, give or take--that’s why I thought of him.

He was actually a year younger than me and was still in high school, so he was at home when I went. I made some excuse to my parents about picking up more of my CDs--which was true--but went to see Eric. He was glad to loan me some of his girl clothes. He laughed his head off at the bet. Then he asked about my side of it. I told him.

"You? Are going to get naked? I don’t believe it!"

"Yeah. God, I hope the Red Sox sweep!"

"You know I’m a Sox fan, but it’d almost be worth it to see you naked."

"What do you care? You’re gay!"

"Not gay, really," he said.

"Excuse me? You told me you were gay and a drag queen four years ago!"

"I’ve decided I’m more bi. With a leaning towards guys, mind you, but...well, remember Tara Rienke?"

"Yeah."

"We had sex last weekend. And it was fun. We’re sort of dating, actually. So I guess I’m bi."

My mouth just dropped. "Oh this just beats all doesn’t it? My best friend, who is supposedly gay, loses his virginity before I do! I think I’m going to go scream now!"

Eric laughed. "Hey, my parents don’t have me on a leash."

"True. Well, mine don’t anymore."

"There you go. Maybe you can get naked for this Vinnie guy and then do the nasty."

"Not hardly! I’d rather sleep with you," I said, teasing.

"Oh, you sound so enthusiastic," he laughed.

-----------

As I drove back to campus, I couldn’t help but think that my life had turned upside down. Me betting my clothes? Eric sleeping with a girl? Yikes.

I was completely unsettled. And it didn’t get better as Tuesday, and game one, approached. At least game one looked like it was in the bag with Schilling pitching.

I went to Vinnie’s room--Mitch came down to ours--right before gametime on Tuesday. Vinnie was, at least, cordial. He had sodas and munchies out, and offered me some. He and Mitch had a couch in their room--he gave that to me and sat in the chair at his desk.

"So, you ready to start taking clothes off, Princess?"

"Not with Schilling on the hill. And would you stop calling me that?"

"What am I supposed to call you?"

"Duh--how about trying my name?"

He grinned at me. "I’m sorry, I just can’t call you Freddie. Just can’t do it. I mean, I’ve got an Uncle Freddie. He’s actually my great-uncle. He’s a 65 year old Sicilian man with an accent, stooped shoulders, and garlic breath. He pats me on the cheeks and calls me Vincenzo. You are not a Freddie. You’re way too cute."

I was secretly pleased at the too-cute thing, but I said, "Well, what about Frederica?"

"That makes me feel like I’ve been plunked down in the middle of the cast of Amadeus." I cracked up at that. "What were your parents thinking, anyhow?"

"That my great-aunt Frederica would put them in the will."

"Ah. Figures. And you’ve got a great-aunt Freddie to go with my great-uncle Freddie. So, what’s your middle name?"

Oh, God. "None of your business."

"Come on, Frederica. Fess up."

"OK, Fine. Van Haaken. My mother’s maiden name."

"Frederica Van Haaken Montclair. Jesus. That name has its own tax bracket, I think. Princess it is, then."

"I’m never going to get you to stop calling me that, am I?"

"Let’s face it, it fits," he grinned. "Come on, Frederica Van Haaken Montclair, embrace your inner Princess."

"You’ll be embracing yours when I get you all decked out in women’s clothes."

"Not gonna happen," he said. "Nope. I’m sure I’ll get a bra and panties somewhere along the way, but you are going to be the one fully disrobed by the first game of the World Series. Count on it. And, by the way, Princess, I misjudged you. I figured you were too pristine to take that bet. Didn’t figure anyone had ever laid eyes on that body yet, what with you being a Princess and all."

I admitted it. "Nobody has."

"Scuse me?"

I forced the words out around the knot in my throat. "If I should lose the bet, you’d be the first to see me, you know, that way. In fact, if I lose a game or two, you’ll be the first to see just about anything."

He stared at me. "You’re a virgin, too, I take it? You’re that innocent?" I nodded.

Suddenly, he looked like he was mad. Mad? Why was he mad? "Why the hell did you accept this bet? Why? Jesus, Freddie!"

"Huh?" I said, clueless.

"It’s not right! You shouldn’t be doing any of this for the first time for a bet! It’s stupid!" He took a deep breath. "Whatever you might think of me, I’m not an asshole. I don’t want to be the one to force you to do anything because of a bet. I’m going to let you out of it."

I should’ve been relieved. I should’ve. This is what I wanted, right? I was scared of this bet, right? And I trusted Vinnie, somehow, not to give me a hard time about accepting his offer. I opened my mouth to accept.

However, what came out of my mouth was the truth. The buried truth, the truth I hadn’t been away from home long enough to face yet. It just came out. "Vinnie, I’m not innocent because I choose to be. I’m innocent because my parents are overprotective. I’ve never done anything because I was watched like a hawk, not because I didn’t want to do anything. I’m fine with the bet."

Boy oh boy oh boy, did I actually say that? And I kept it up. Vinnie asked me, "Are you sure?" and I told him I was.

What the hell was wrong with me? Two opportunities to back out, and I didn’t take them?

I was so confused.

Anyhow, Vinnie accepted my answer, and there was no more talk of dropping the bet. There was a while before the game started, so we were just chatting, with ESPN on in the background. "So, what are you majoring in?" he asked me.

"Haven’t decided yet. Probably something liberal arts."

"English or something?"

"Yeah, something like that."

"Nice rich girl’s major."

"Yeah, yeah, yeah," I snorted. "What about you?"

"Math and Secondary Ed. I want to teach high school Math."

"That’s really cool," I said. We chatted about this and that for a bit.

"An only child?" he said to me. "Boy, I would’ve hated that. I have two brothers and two sisters. It was loud in my house but it wasn’t ever boring."

"I can imagine," I laughed. The more we talked, the more comfortable with him I became. I was beginning to think I misjudged him. He wasn’t stupid, not at all. And he was funny, he had me laughing a lot.

The game came on, and he joined me on the couch. We’d made some popcorn and were munching on it. "There he is, Mister Curt Schilling," I said. "I’ve got your bra all ready."

"Ah, well, I don’t count on a sweep, I figured I’d at least get into the bra. I just think you’ll get out of more."

"Don’t count on it." The game started, and we settled back to watch it.

And it became very clear that all was not well in Red Sox Nation. The Yankees got two runs off of Schilling in the first. And it was plain right away that this wasn’t the sometimes-unhittable Curt Schilling that we’d seen all year, that he’d been in his entire playoff career. "Something’s wrong with Schilling," Vinnie said astutely.

"Oy. I think you’re right, but, God, I hope it’s not the ankle," I said. He’d been battling bad tendonitis in his ankle for weeks. He got through the second, but the wheels fell off in the third.

"It’s got to be the ankle," Vinnie said as the Yankees piled up the hits. "I’ve seen Curt Schilling pitch a number of times. He’s got no drive with that back leg today."

He was right. Schilling was way off his usual on the radar gun and the Yankees were teeing off. It was six to nothing before the end of the third inning. Schilling came out, and the bullpen let it get to 8-0 before the Red Sox even got a baserunner.

Then they made it interesting. They actually got seven runs between the seventh and eighth innings, to get to 8-7. But then the Yankees got a couple more, and that was that.

Oh, man, it made me sick. We needed the Schilling games. Flat-out needed them.

"That’s one. And tomorrow the Yankees get to be Pedro’s Daddy again."

"Oh, God, don’t remind me," I sighed.

"And I get to see some skin. I’m looking forward to it." Oy. And I had the opportunity to get out of this! I must be nuts.

"I’ll bet you are. Pervert."

"You know it. I’ll bet all you own is those boring plain white Grannie bras, but I’ll enjoy seeing what’s underneath peeking out."

"Huh," I snorted, and stormed out of his room. "See you tomorrow," he called after me, entirely too cheerful about it.

Damn. This guy was going to see me without a shirt tomorrow.

And--he was right--in a plain white Grannie bra.

Shit.

Earth to Pedro Martinez. Earth to Pedro Martinez. You better pitch the game of your LIFE tomorrow!! Two articles of clothing in the first two games would be too much.

Especially considering my panties were as boring as my bras.

Shit.