Doing a sleazy thing, for a higher price

The town you've claimed as your new temporary home is a town that runs along a wide and powerful river. Trade is very lucrative across such bodies, and the ample fishing and farming helps support the population here. You're not fond of the taste or the smell of such ghastly terestrial foods, but there is plenty else here to be found with the coin.

Coin is something you have a shrinking supply of, but there's an answer for that. You walk into an establishment after sunset, a large inn, with a wooden sign showing it's name, The Inn You End O. It looks as though there was originally a full word at the end, but that it been burned and became illegible, but you ponder as to whether that was deliberate to create something of a pun. Though the place was large by the standards of most inn's, it was still crowded on the main floor, full of people enjoying their stouts, evening meals, and friendly company on the main floor while the rentable rooms were on an upper level, with the doors facing the bar so that it's halfling owner could easily see who's coming or leaving. You had already rented a room here, and hoped to make good use of it.

Despite this being a merchant town where people transited through often, it was still rare for someone to see a Drow in these parts, and you attracted a deal of attention as you entered, just as you had hoped. You take a spot at the corner nearest the front door, leaning against the bar with your elbows. Bending at the waist to do so causes your long legs and shapely butt to stick out. You feign an innocent, absent minded swaying to help entice onlookers, which you keep an eye out for with periphreal vision. You see a small commotion out of the corner of your eye, as someone stands up from a group at a round table, and approaches you, with all the exuberant confidence that is typical in young men.

"Hey there" he started off innocently enough "I don't believe I've seen you in here before"

"I don't believe I've been in here before, no."

"That explains it. I know I'd remember seeing someone as beautiful as you"

"You're too kind." You reply modestly. The man was frankly unexecptional to look at, just another seeming average member of a merely average race.

"Sam Brooks" he extended his hand in friendly handshake, which you courteously replied "Mysilghana. I've lately taken to be called Missy by your kind."

"Well, Missy, what brings such a tall, dark, and lovely figure like yourself through these parts?"

"You first" You reply with your best smile "I'm sure your story is less depressing."

"There's nothing really to it, actually. Just part of a small merchant caravan with my friends over there in the corner." He makes a small nudge with his head, keeping his eyes on you "just trying to branch out my families business prospects."

Just what you were hoping for, he's traveling with money to burn, and friends to impress. "Is that all you hope to accomplish on your travels?"

"That's what I'll be telling my parents on my return, yes, but that's not all on my mind. I'm sure you've heard the old addage of the journey being more important than the destination right?"

"Of course"

"Well, why don't we make this journey a memorable one, for both of us?"

You smile in response, though not for the reason he thinks. You straighten up and scoot in only inches away from him, brushing his arm for a second. Predictably, his entire head moves down to see your hand. The closeness is breaking his fragile confidence, it's lovely to watch

"Tell me, mister brooks. This is the first time you and your friends are traveling without your parents, right?"

"Ya, why do you ask? we've done this route plenty of times before. We know what we're doing."

"I don't doubt it. I'm sure you and your friends are very capable, and you want to prove those capabilities, to your parents, and your friends."

"Sure, who wouldn't?"

"Indeed, and along the way, you want to enjoy some of the privileges of being an adult, of being a strong, capable, independent young man"

"Ya" His eyes get a little wary "I mean, again, wouldn't anyone? This is our chance to finally get out from their shadows, out from their rules, to do the things we want to do without anyone telling us no."

"Which means, I'm guessing, that I would be your first, if I took you up on your proposition"

The wind came out Sam's sail, as he recognized now what he unintentionally admitted. "Well, ya, but that shouldn't matter."

"And it doesn't" You gently place a finger towards his lip, "Not to me. I just want to know what I'm getting into. You want your first time to be an event, and you want to show off as a lady's man to your friends. I'll abide that, if the price is right."

He scoffed for a moment at the notion of paying for sex "You mean, you're a prostitute? You're really willing to pretend to like me for money?"

You move in close and exhale hot air into his ear, before moaning and whispering "I'll let you pretend anything you want Sam. I'll do anything you ask." You hear a clang of metal on wood. Pulling back, you see ten shining gold coins on the counter, and Sam's hand, that had just slammed them down.

"Good boy" You say with a smile "You won't regret this." You discretely take the coins and tuck them away. Before you lead Sam to your room, you hand him something small into the palm of his hand. It looks like a large pearl, but is soft and squishy to the touch

"Swallow this. You'll thank for it later."

"Why what is it?"

"It's a surprise, just trust me."

"How do I know it isn't poison?"

"Because I'm that bold or that dumb to just hand a victim poison. Besides, how I know you won't kill me in the act? It's not to our benefit, and not in either's nature, now come on." You finish the questions now before it ruins everything, and lead him to your room. His friends still at the round table by the stairs, you make a small gesture to grant Sam credibility.

"Don't wait up boys" You say with a loud voice and a seductive smile "Sam's going to be up for a long time." There's low laughter and even a whistle as you lead your partner up the stairs, and into the room. With the door closed behind you, you see that veneer of confidence melt away. Sam's eyes move from you to the floor and back, he fidgets with his hands in front of his chest, and he swallows hard.

"So, uhhhh, how does this work?"

"Well, it works when the male takes his erect penis and inserts it in the vagina of the female, eventually producing offspring."

"No no no no, not that. I understand that part, but I mean, you know. How does this all start off?"

"Well, Sam, you bought me for the night, so it's really up to you. You could just shove your cock down my throat, cum after a few seconds, and be done with it. Or," as you teasingly remove your clothing "You could take it slowly, and really savor the experience."

Sam's eyes are mesmerized by your body and bare skin. "You've never seen a woman naked, have you?" You don't wait for the answer "Do you want to touch?" You cup your breasts in your hands to tantalize him. Sam approaches slowly, his hands out in front of him. He lingers for a few seconds, looking at you before he touches you. It's ironic, you think, that he boasted of wanting to be so independant and void of rules, and yet is so cautious about breaking rules that don't actually exist. His hands move across your chest, relishing in your soft, smooth skin, giving your tits a firm squeeze. You moan slightly as he pinches each of your nipples between his thumb and index finger. Slowly, he bends down and cranes his neck, choosing instead to suckle on one of them, flicking it with his tongue. Your fingers comb through his hair in gentle encouragement. Despite this being his first time, he seems to understand at least some things about pleasing women. He struggles to multitask; taking his pants off while also playing with your tiny nipples, and eventually gives up on the first.

You take some joy in seeing his cock as it's freed. Like most humans, his is longer and thicker than those belonging to Drow or your other Elvish cousins. In the cool night, his balls quickly pull back to his body.

"Misy? Would you? Would you put in your mouth?" His nervousness is approaching on tiresome, but you push those thoughts down.

"Of course Sam." You say as you pat his head again, before giving him a long and passionate kiss with your tongue. You slowly drop to your knees, looking up at him deeply with your darkened eyes.

"Like I said" You hold his cock up by the base and give it a slow stroke. You move your lips close to his shaft, kissing in it in different places with each word.

"Anything"

"You"

"Want"

With the last word, you wrap your soft lips around the head of his cock and begin to suck on it, moving your head up and down slowly. Sam moans loudly, in complete ecstasy from his first blowjob. Like you said, you intend to give it to him soft and slow. Even if it would be in your best interest to just **** this as quickly as you can, you are slightly sympathetic. The first time should be special, and you're certainly going to make it that for him.

That is, unless Sam commits self sabotage, which seems likely. You feel him grab you by your hair and push you further down his cock. Than faster. His moans grow, and as he finds it more and more pleasurable, the further he pushes it. In no time at all, he's got you in both hands, pummeling your throat with your cock. His moans grow louder and louder, as he tries to keep his orgasm back as long as he can. Pulling out of your throat, he strokes your face still with one hand and strokes himself with the other, needingonly a couple of seconds before he cums. You let out practiced moans as thick, salty strings coat your face. If it helps men think you like it, than so be it.

"mmmmm, good boy" You let out in encouragement "You're starting to get it."

"That felt amazing, missy"

"And that wasn't even the best part..." You lift up on your knees, so his cock rests between your tits. You slowly move back and forth, letting his wet member slide on your skin. "You're still rock hard Sam. Time for you to have the real treat." You get on the bed on all fours, facing the headboard, exposing your eager holes to your partner. Sam seemed to stare again as he approached, never having seen a pussy up close before. He was slow to man up and push himself in, but you had to admit that it felt pleasurable to you as well once he finally did. This position was great for two reasons. It let Sam have total control, both in how fast or how hard he fucked you, and giving him opportunity to grasp at your hips and ass along the way. The other benefit was for you; it allowed you to close your eyes and pretend it was someone else, not that you had anyone in mind tonight.

Sensitive from having just recuperated from his first ever blowjob, and going immediately to his first ever pussy, Sam was slow moving, taking a long stroke. He pulled every last centimeter of the cock out of you, before pushing it again slowly, all the way to the base.

"So, what do you think, big boy?" You ask sexily as you turn your head to the side

"Worth every penny Missy." As he responds, he picks up and finds a steady pace, with the rythmic sound of his legs and pelvis against your ass filling the room.

"I'm glad to hear it. Make sure you walk away satisfied."

"What about you, Missy? Is this good for you too?" His concern for the other partner is endearing and would serve him well if he ever had a girlfriend or spouse. This isn't that. Still, you give the encouragement and validation he clearly needs.

"Oh ya" You let out as you start to move your hips, against his rhythm "This cock is really working me good." His hands instinctively held on at your hips. Out of nowhere, you feel an almost painful swat as he spanks your ass. You were about to chastise him for it, but you remember what you told him, and take in stride. The next one stings even more, and by the fourth or fifth spanking it seems like he's giving more energy in his hands than his cock. If that's what he wants, fine, but you're after more enjoyable things. With each smack, you try to push against him harder, to get him to focus. It takes a little while, but he gets the idea, and stops the slapping. Like before with the blowjob, starting to go harder only encouraged him to go even more, and before you knew, he was fucking with everything he had, and you did what you could to keep up. Another loud groan bellowed out of Sam as he came again, this time deep inside you. Exhaustion setting in, he lowered himself on top of you. Struggling with his weight, you clumsily rolled him off of you as you fell into the bed yourself. Rolling on his back, you were able to see that Sam's cock was still ready to go, even after what he just did. The thin sweat around his whole body suggested that the rest of the body disagreed.

"I'm just going to rest here for a second Missy, if I can."

"Of course. Take your time" You say with soft reassurance, pulling the thin blanket over you both. You were sure he was going to pass out here for most of the night, and that was okay with you. Virgins could be troublesome to deal with, but you saw that he had charm and positive traits that another of his race would find desirable in a long term partner.

Which made you all the more glad that he would be leaving in the morning. The young man could fuck, but that was probably his own redeemable trait in your eyes. Still, you got a decent amount of coin for the trouble, more than enough to get you started again in your real profession.