On the dumbometer this rated at least a ten, maybe even higher. I pushed myself up from the table and took a deep breath before turning toward the table where she was sitting. It was a stupid bet, or dare, whichever you wanted to call it. In my fifty years on this earth you'd think I would have learned not to get baited like this. John and Eddie were like two little children even if they were in their thirties.
Having to go to the five-day conference was an inconvenience, having to go with these two middle-age juvenile delinquents was almost torture. I'd had to deal with these two at work for several years, but this was the first time I had to bring them to this conference. The conference had so far been pretty interesting, it was the afterhours that was difficult.
Between bar hopping and strip clubs, my two younger cohorts found no end of ways to try and embarrass me, while they seemed to be totally shameless. Tonight's game seemed to be destined to cause me even further embarrassment. Three beers into the early evening I allowed myself to be goaded into taking the dare, now it seems I would have to pay the piper.
At least she wasn't too young, probably my own age. And she was most certainly good looking! Long blond hair, curvaceous body with probably thirty eight C or bigger breasts that filled out the snug cream colored dress sexily. Even from across the room I could see the two bumps formed in the front of the dress by her nipples, leading me to think that her breasts were bare under the thin fabric. She was quite the looker; a fact my cock was already alerting me to. It didn't really matter though, the glittering little band on her left hand pretty much meant that she would refuse my request no matter how I framed it.
But now it was my turn. While John had succeeded, Eddie had failed in his attempt, as expected. You can't just walk up to a woman and ask her hand over her panties! Well, that was of course the basis of the argument, bet, dare, whatever. They had done just that, with Eddie coming up empty. I was surprised John succeeded, but then the random draw left him with a young, sexily dressed, half-drunk woman that I probably could have easily talked into going to my room or anywhere for that matter. Now it was my turn to prove that a smoother approach would provide results. I was a bit surprised by how sexily the woman was dressed for the small hotel bar and her apparent age, but again, the glittering band on her left hand pretty much doomed me to failure. There was simply no way I was going to talk her out of her panties in a busy hotel bar!
"May I join you for a moment?" I asked her as politely as I could muster with three beers to my credit in the last hour.
"To what end?" She asked, setting down the mixed drink she was nursing and the magazine she was reading.
"Well, to be completely honest, I'm trying to teach my young friends there a lesson, but I'm afraid that they have doomed my attempts to failure. I would at least prefer not to be sent away without even getting to sit down."
"I've heard a lot of pickup lines, but I have to say, this approach is unique. Please...sit down and tell me more." She answered with a smile, waving to the chair across from her.
"Thank you." I answered her with an equal smile, settling in the chair across from her and setting my beer down on the table.
"So. What attempt is doomed to failure?"
"I was trying to tell my young colleagues that today's younger generations simply have no concept of tact. They bull in at full speed and as a result are rebuffed soundly. Their bet, or dare or whatever you might call it was intended to show them that if one approaches a woman with a little respect, that one might at least stand a chance. Fortunately or unfortunately, depending on how you look at it, I drew you as my subject, which of course is doomed to fail."
"And why would your attempt at whatever it is, fail so surely?" She asked curiously.
"Your ring. It's simply impolite to even consider asking a married woman to let me have her panties, especially in a public setting such as this," I answered her. "So I'll thank you for the short but pleasant conversation and go back and pay my debt." I said, picking up my beer.
"Sit down, please." She said with a smile as I started to rise from my chair. I shrugged and sat back down. "I've heard a lot of good pickup lines in my years. But this...this is truly entertaining." She said with a soft chuckle. "So the deal is, you walk up to a strange woman, ask her to take her panties off and hand them to you, and then you what, return to your table victorious?"
"Something like that," I answered a bit sheepishly.
"And if you fail?"
"I have to buy the next round and my prowess with women is forever tainted," I answered her.
"I see. And you're proud of your prowess with women?" She asked, clearly amused.
"Actually, I wouldn't go that far." I answered with a frown.
"So you would allow your young friends to goad you into trying to bed a woman outside the sanctity of your marriage?"
"Well, actually not. The bet is only to obtain her underwear," I answered.
"Hmmm. And your friends chose me? Were there other potential targets?"
"There were three in total, and we drew straws to see who took which target. I'm happy to say that you were my lot."
"And the other two women?"
"Both younger, and attached from what I understand, however my cohorts in crime may still find some success with them later, based on their responses, though one did manage to get her underwear. Without even leaving the bar on top of that."
"It sounds like an interesting little game they chose. Too bad you feel that you too will be unsuccessful."
"I was reasonably sure at the outset that I would, so, I will take my leave and apologize for any embarrassment I might have caused."
"You seem to be in an extraordinary hurry to leave. You don't want to at least attempt to compete your quest?" She asked with a crooked little grin.
"In that case. Might I inquire as to what type of underwear you are currently wearing?"
