Dumb Dare

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?"

"You may inquire. But who says I'm wearing any at all?" She asked with that crooked smile again. "Tell me, is there a time limit on your attempt? Must it be done in a given period of time?"

"None that I am aware of." I answered.

"Good. Tell you what. There's a river just on the other side of the parking lot with a nice walking trail. I'd love to explore it on a wonderfully warm moonlit night, however a lone woman would be an inviting target. Now a couple taking a nice walk along the river would be much less of a target, and I'd be willing to bet that somewhere along the way you might find a way to obtain what you seek. Now, does that sound interesting?"

"That depends on the answer to one question." I said.

"And that is?"

"What would your husband think of this?"

She smiled widely and leaned toward me across the table. "I suspect that in this particular case, my husband would be quite happy to have a protector along with me, and if it costs me my panties, well, I'm sure, in this particular case of course, that he wouldn't object."

"In that case, would you care to join me in exploring the trail along the river? I hear it's an interesting walk."

"It would be my pleasure." She said as she stood up. I stood as well and let her loop one of her arms in mine and then let her steer me back toward the table where Eddie and John were still sitting, watching my progress. She walked right up to the table and leaned down to talk to them quietly. "Your friend will be back. I told him if he plays his cards right he'll most certainly collect on his little bet by his own hands. If he's lucky, he can show them to you tomorrow."

"Oh shit." Eddie groaned as she straightened up, squeezing my arm with hers as she again started to walk. We made our way out of the bar and then the front doors of the hotel before she spoke again.

"So, what shall I call you, besides horny?"

"Mathew. Or Matt. Your choice. And you?"

"Tiffany... Or Tiff if you prefer," she answered.

"So Tiffany. Are you here for the conference?"

"It is what brought me to town. However, if you're planning on talking me out of my panties you might want to pick a different topic."

"So be it. Tell me Tiffany? What's your favorite hobby?"

"Much better. I love to read, but you already guessed that, didn't you?"

"I did. Let's see if you can guess mine?" I answered her with a smile as we stepped off the pavement and onto the grass. "Looks like the river trail is down this way."

"It does seem that way. Let's see. Your hobby. This could be difficult. You clearly are well educated and work in a highly technical field, or you wouldn't be here. You're good with your hands and frequently work with them. Yes, I can tell by the numerous small scars. If I were to guess I'd say you make things out of wood."

"Good start. I do enjoy making furniture. But that is most definitely not my favorite hobby."

"I know. I just thought I'd drag it out a little for fun. Are you enjoying it?"

"I am."

"Good. Your hobby, if I were to guess, is that you write. Probably fiction of some type. Possibly science fiction?"

"You're danger close," I answered with a smile as we stepped onto the winding asphalt path. It wasn't too large, but wide enough for the two of us to walk side by side. I could see that it wound along the shoreline with what looked like frequent little cuts that you could step down off the path into circular sitting areas that overlook the flowing water a few feet below. There appeared to be several of these before the trail disappeared off into the darkness, the only light for us to walk by being the quarter moon and lights bleeding in from the city around us.

"Close? That's a surprise. Which part was wrong?"

"Well, technically you're right. I do write and I do write science fiction. But there is another type of fiction I enjoy writing even more."

"Hmmm. Now this is a puzzle. Another type of fiction, yet I suspect that you are careful to keep that separated from your other writing. This leaves me somewhat stumped. How about some type of hint?"

I smiled and led her off the path into one of the somewhat secluded concrete pits, guiding her to a stone bench seat. The little nook was about ten feet in diameter, with rock and stone walls about three feet high, lined with stone and rock benches. The nook overhung the water allowing us to look over the edge at the meandering river only a few feet below. In the moonlight her cream colored dress seemed to almost glow, the very short hem hiding her panties but had ridden up enough on her thighs to not quite hide the tops of the stockings encasing her long muscular legs. She stood almost the same height as I did in her heels, the top of her dress molding itself to her breasts and held up by only one small string looping around her neck. She sat on one of the stone benches and then turned to look at me, waiting for me to respond.

"Let's see. How does this sound? He pulled her close, pulling her body to his, feeling the softness of her breasts press against his chest as his strong arms circled her. She could feel the heat of his body against her as his hand worked slowly down her back his fingers stroking her lower back and then the curve of her firm round ass. She felt his hands bunching her skirt, slowly pulling it up, working it ever higher until she felt his fingers find her bare skin beneath. She sighed softly as his strong hands gripped and teased her firm ass cheeks, his fingers working all the way down her round globes until his fingers teased the tops of her stockings and the fingers of one hand threatened to slip between her legs from behind."

"I see. Erotica. Very interesting. And from the sound of your short adlib, I'd say you are quite good at it."

"Thank you." I said with a nod.

"So. You started to write a wonderful little piece. Suppose you show me how you might finish it?" She coaxed, standing up and waiting for me to rise with her.

I stood up in front of her and wrapped my arms around her, letting my hands pull her gently and then more tightly to me as she wrapped her arms around me as well. I felt her hands working up and down my back gently while I bunched the skirt of her dress up in my hands, working it higher with each grab of the creamy yellowish material. The snug dress clung to her waist where I had bunched it, allowing me to stroke the bare skin across the top of her firm cheeks. I heard her sigh softly as my fingers found a lacy band low across her buns, my fingers worming into the waistband of her panties as I worked my hands lower. I let my fingers push the material down as I slid my hands further under her firm round cheeks and squeezed each firm round mound. I continued working my fingers down, blatantly pushing her panties down now, working them gently down to her thighs, my fingers teasing the tops of her stockings and then, as in my quickly thought up story, between her legs to feel her wet pussy lips.

"Well, now you know that I'm am wearing panties." She said breathlessly, pushing herself away from me, her dress around her waist and her panties around her thighs. "But I'm not that easy. If you want them you're going to have to buy them!" She said before practically running up the three steps to the asphalt trail and running down it, albeit slowly in the high heels, giggling, looking back to make sure I was following her. In the dark I could see her dress, her bare creamy ass and her long nylon encased legs as she ran down the trail ahead of me.

I followed her down into the next pit, arriving after she had already settled herself on the rock wall. Her bare ass on the rock and her legs bent and held up in front of her with her knees together. "Now. What would you pay to put these sexy little panties in your pocket?" She cooed softly.

"Well, it would seem that money isn't what you desire. Tell me oh seductress. What is your price?"

"Two." She said simply.

"Two? Two what?"

"I want you to make me come twice, two different ways. I'm quite sure that a writer of erotica can find two ways to make one incredibly horny woman come." She said in a soft sultry voice.

"I'm sure I can." I answered, stepping to her and reaching for her panties. She grinned at me as I slid the panties down her legs and worked them off over her heels. I held them up for her to see before putting them in my pocket. She spread her legs, letting me see her mostly shaved pussy, only a small triangle of tight blond curls on her mound pointing toward her full round lips. I could see that she had an abundance of inner lip protruding, smooshed against her outer lips by her panties. I reached a finger down to her pussy and slowly teased my finger down her lips, gently spreading them and letting them protrude more naturally in the moonlight.

"I was hoping you could find a more imaginable way to make me come than teasing me with a single finger." She said with an exaggerated pout.

"I haven't even started yet. I was just admiring the sexy parts I have to work with."

"And what is your conclusion?"

"That it looks like a very sexy and tasty pussy." I told her as I squatted down in front of her. "I wonder. If I do an exceptionally good job, how do you feel about returning the favor?"

"It would take an EXCEPTIONALLY good job," she answered with a grin. "Think you're up to it?"

"We'll certainly find out," I answered as I moved my face between her legs. I smelled the scent of her arousal, as I reached my tongue out and dragged it slowly up between her lips. I stroked up to the juncture of her flowery soft lips and searched out her hard clit.

"Ohhh that is definitely a good start!" She moaned softly. "Keep starting just like that."

"Oh I'd never be so boring as to do the same thing over and over." I said jokingly as I dipped my tongue deep between her lips and slid it up along her pubic bone. I found her clit with the tip of my tongue again and flicked and circled around it for several seconds before moving down for another stroke. I wrapped my arms around her thighs, using them to spread her legs farther and my fingers to gently spread her lips. I teased my tongue up and down her now spread pussy, teasing deep, almost pressing my tongue into her tunnel entrance and then teasing just the edges and tips of her lips. Not to be left out, every few strokes up her wet lips I concentrated on her clit, flicking and licking it until she couldn't keep her hips still. Over and over I teased her pussy, inching her closer to climax, and then letting it slip away slightly.

"OH FUCK!" She cried loudly, gasping again as I closed my lips around her clit. "OH please. Make me come!"

"As you wish." I answered her with a smile. I moved one arm from around her thigh and pushed one finger into her, rolling my hand palm up and stroking the inside of her tunnel as I teased my tongue across her clit, flicking it quickly with just the tip of my tongue. I heard her gasp and try to hump her hips up toward my face, her breathing ragged and her legs starting to tremble.

"Ohhhhh god yes god yes god yes." She moaned loudly as her velvety soft tunnel clenched around my finger, her whole body giving little jerks and shudders as her climax washed over her. "OHHHH JESUS!" She squealed as I closed my lips around her clit and sucked on it, making her whole body buck hard in front of me. Her hands grabbed at my head and alternately tried to pull me toward her and push me away before finally deciding to push.

I pulled my face from her pussy and took a breath, letting go of her leg and rocking back on my heels. "So how was that?"

"That was...oh god yes. It was Sooooo...Fuck." She said breathing heavily. "Help me up!"

I reached a hand out and helped her off the wall to her feet. She grinned at me and then ran past me, up the stairs and down the path into the darkness.

I followed along, pausing only when I found her dress in the path. I picked it up and ran down the path to the next little seclusion and down into the depressed rock circle.

Tiffany was sitting on the wall edge, naked except for her stockings and high heels. Her skin glowed softly in the shafts of moonlight filtering through the branches of the trees overhanging the little rock nook.

"You held up your part of the bargain, but you're grossly overdressed." She said with a giggle. "Now just how do we solve this?"

"I'm in your hands." I answered her with a grin.

"You are." She said, pushing off the wall and stepping to me. She tugged on my polo shirt, pulling it out of my pants. She worked it over my head and tossed it aside, letting it land where I had dropped her dress. With a grin she squatted down, untying my shoes and then lifting her hands to my belt. She grinned up at me, the moonlight lighting her face as she spread the front of my pants and pulled my cock from within, my shaft already rock hard.

"Well, look what we have here," she cooed as she pulled my pants down to my knees. She wrapped her lips around my head and swirled her tongue around and under my engorged head as her hand slowly stroked my shaft. I let my hands stroke her long blond hair as she bobbed her face on and off my shaft, driving my cock in and out of her mouth, her hand following her lips. She slowed her strokes and pushed her face toward me, driving as much of me into her mouth and throat as she could, drawing long groan from me.

All too suddenly she pulled her mouth from my cock and stood up. "Last call. I'll be waiting in the next one of these. If you're as naked as I am you can take me once any way you want." And then with a giggle, she ran up the stairs and down the path.

It took me far too long to pull my shoes and pants off and then get my shoes back on. I picked up our clothes and followed along, quickly walking to the next little nook and down into it.