My roommate, Rob, used to work for a small engineering company. When I say small, I mean his boss was the engineer, he was the draftsman and the only other employee was the receptionist. Since the boss was usually out getting the work, that left Rob in the office doing the work. Consequently, he spent a lot of time with the receptionist.
When Rob started telling me about the new receptionist they'd hired, Lisa, I thought things sounded good for him – she seemed to be quite a flirt. Little did I know at the time that hiring Lisa would be beneficial to both of us eventually. Rob would come home and give me the latest each day after work – Lisa did this, Lisa said that – but one day he had even more interesting news. Turns out Lisa is good friends with Dawn, a cocktail waitress at one of our favorite watering holes whom Rob had briefly pursued in the not-too-distant past. I didn't know if this was such a good thing because it looked like things were going well for Rob with Lisa. The last thing he needed was Dawn to distract him and take away his focus – a bird in the hand is worth two in the bush, as they say.
It ended up I was worrying for nothing. If fact, I think Rob may even have had ideas of trying to hook me up with Dawn. The four of us got together for drinks one evening and had a really great time. Dawn and I didn't hook up, but then neither did Rob and Lisa. Instead, we spent the evening laughing and joking like we had been hanging out together for years. We had so much fun that it didn't even bother me that things weren't leaning toward the romantic. That's not to say that I didn't find Dawn, or Lisa for that matter, attractive. On the contrary, I wasted plenty of time daydreaming about what I would love to do to either or both of them.
As time went on, we got together every now and again and always had a great time. Nobody was pushing for anything to go farther, though Rob and I talked about how sweet it could be if it ever happened. One Saturday in December, we finally crossed that line and never looked back.
Lisa and Dawn had come up by us to go Christmas shopping. It was a cold, gray day and after a few hours of going from store to store, we headed back to our apartment to warm up. We made a big batch of hot chocolate and were sitting around listening to music not doing much of anything when Dawn said, "I think this day is trying to put us into a funk. Let's do something fun."
Rob jokingly suggested strip poker.
"We would so whip your butts," Dawn challenged.
This wasn't unlikely – neither Rob nor I was much of a card shark, but they didn't know that. We did know how to keep a poker face, though, and how to get their competitive hackles up. We jawed back and forth about who'd be whipping whose butts until no one dared back down. We broke out the cards, set some ground rules and settled around the table.
It turned out we all pretty much sucked at poker and pretty soon none of us was wearing much. Rob and I still had our jeans and underwear on when Dawn lost her bra. Lisa was already down to just her bikini panties at that point. It was so erotic seeing them gradually shedding their clothes and I had almost blown a load in my pants when I got my first look at Lisa's naked boobs. They were probably 36C's topped with big pink aureola and hard nipples. If the tabletop had been glass they would have seen my rock hard rod straining against the zipper of my Levi's. Of course if the tabletop had been glass, I'd have been able to stare at them in their bikini panties for the past ten minutes and there'd probably be a wet spot on the front of my jeans.
Dawn slipped out of her bra, freeing her lovelies. I'd guess 34C – she was smaller than Lisa, but she was also a smaller girl so they looked nice and big on her small frame.
"So what happens after we get one of you naked?" Rob piped in.
"Rob, you'll be naked long before either of us." Dawn responded confidently.
"Oh, so you're going to start playing now?" Rob shot back.
"You're dead now, Mr. Naked. Pretty soon we'll all be straining to see your tiny little penis."
Things were getting ugly now, so I threw down a challenge.
"Okay, if you're so confident," I said, "how about we make this interesting. If either of you guys wins, Rob and I will both strip off our jeans but..." and here was the interesting part "if one of you loses, you both lose your panties or..."
