Allen (starting off well)

OOC for this particular thread's characters.

Lee, the hostess, 22, bi-sexual female.
Alice, 26, Lee's married neighbor.
Allen, 18, Lee's heterosexual, virgin cousin.
Betty, 19, Lee's lesbian lover.
Brian, 24, Alice's husband.

I couldn't believe that we were actually going to do this. I'd heard from one of Lee's former girl friends that she and the 'Giggling Girl Gang' -- a group of female friends who all happened to be into other females -- had played this often. But I'd always thought it was just their way of teasing me when I was trying to hang out with them and ogle some beautiful female parts.

I just thought they were trying to 'get a rise' out of me, not that any of them would be interested in the resulting erection. More than once their teasing had caused me to politely excuse myself -- to do this task or that -- and hurry home to my bed and bottle of hand lotion.

I glanced around at the other players and wondered what they were going to look like naked. Clothed, they were all a good-to-great looking bunch of people. You had to hand it to Lee: she had a way of surrounding herself with beautiful people, men and women, gay and straight.

"Let's begin," Lee said, and having already won the right to roll first, did so. "Seven. Chance."

She moved ahead, drew a card, and grimaced. "Advance to Go. Collect $200."

Around the board, the reactions were mixed, from grimacing grumbles to ecstatic cheers. I didn't understand the reactions until I saw Lee paying the bank $200 and remembered her explanation that if a Chance or Community Chest card told you to collect money, that you actually had to PAY it instead.

"Next," she said, handing the dice to me.

I rolled a five, advanced to Reading Railroad with a broad smile, and forked over my $200. Play continued around the board until it was my turn again. I rolled double 5s, bought Pennsylvania Railroad, then -- amazingly -- rolled double 5s again!

"Three railroads!" Betty groaned. "He's going to strip us bare in no time."

I chuckled to myself, for obvious and less obvious reasons both. With three railroads, I would be collecting $100 each time someone landed on them, a nice little sum for a $200 dollar property. That was the obvious reason.

The less obvious reason was that it was Alice -- Lee's lesbian lover -- was the first to realize the danger ahead. Alice was one of the sexiest women I'd ever met, and I'd often fantasized about losing my virginity to her, despite being fully aware of the fact that Alice had no interest in that which was dangling between my thighs.

To make things even more impossibly fantastic -- and socially inappropriate -- many of those fantasies had included not just Alice but my cousin Lee as well. How many times had I beat off in the shower or under the sheets to the imagining of the two of them kissing and caressing and groping and 'mounting' my body, driving it to a multitude of orgasms...?

"I think y'all are missing something," Lee spoke up, pointing to my newly claimed property deeds and diminishing cache of money. "While you have to have properties to collect rent and, therefore, keep your clothes..."

Giggles, chuckled, and crude comments cut her off for a moment before she continued, "...you have to remember that it takes money to buy them. Money that you can't replace by passing Go."

I looked at my money and realized just how much of a hit buying the properties had been. In just two turns, $600 of my initial $1500 were gone. I needed the properties, of course, but I also realized that if my initial good luck held, I was going to have to start shedding clothing to buy them all.

And it wasn't bad enough that I'd be naked before these people, which included friends, family and strangers, as well as gays, straights, and 'unknowns'. Worse than that, I'd never BEEN naked with even ONE person before.

What the fuck was I thinking when I agreed to this?