Alanna the Courtesan Pt. 03

The sun always shone outside the palace. Or that's what Alanna thought. And it was a beautiful day today, complete with clear, azure skies, and the hustle of upper class living. Carriages of all kinds went down the street with various symbols in the windows. Being a courtesan, she could use any of these for free. Well, almost free. With a wave of her hand, a carriage with three stars painted along the side pulled to a stop. A man, about thirty and dressed in silks, opened the door. Across him was another man of similar or slightly lower standing, with similar or slightly cheaper clothes. Perfect. Alanna stepped inside and sat right on the lap of the man with more money. He slid his hands around her waist and the carriage took off.

Alanna made small movements in these early moments, just grinding a bit. She smiled just a little as she remembered the first time she'd done this. Back then, she had immediately gone to trying to give a blowjob to the richest man there. She'd thought it would be polite, the least she could do for a ride in such a fine carriage. And of course, he had enjoyed it. The problem was that everyone else wanted the same treatment. That meant giving five back-to-back blowjobs to the other members of that carriage and arriving late to her appointment. For now, all she did was sit on his lap to grind on his hard cock a little.

Out of politeness, she leaned to the side just a touch so the men could continue their conversation. It seemed the two of them must have been used to courtesans, as neither one broke their conversation for even a moment.

"And I'm telling you," The poorer man insisted, "That the longer we tie ourselves to this ridiculous and draconic system--"

"--Ridiculous?! Draconic!? You can't be serious! The only thing ridiculous about it is that the City Guard aren't paid more!" The richer man demanded. Neither one of them noticed as Alanna began to pick up her pace a little. He'd gotten hard, but now it was time to get his attention. Not to mention she liked the idea of letting him release a little bit of that tension.

"Mmm. That is...that is very...." Moaned the richer man as Alanna began to lean onto his erection even more. Across from him, the poorer man looked frustrated. He held out his hand, and the carriage stopped again.

A young woman stepped into the carriage. She had shoulder length blonde hair that flipped up just a little at the ends. There was a small splash of freckles over her nose, which pointed just a little bit upwards. To top it all off, she had eyes as rich and blue as the sky Alanna had just been admiring. Everyone drank her in like parched dogs.              

"H-hello." The blonde teen said as she attempted a small curtsey. "My name is Lyra. I'm very glad you--oh!" She squeaked as the poorer man pinched her butt. While her fine dress and shapely figure could make her a courtesan, Alanna couldn't be sure. Not yet anyway.

"Just please. Sit." The poorer man patted the seat next to him. Which, she did.

"She's a good girl." Alanna thought. Obedient without being desperate. That was a tough wire to walk, even for some of the most skilled courtesans, like herself. Personally, she always reminded herself that she was in power the whole time. The punishment for doing something after she, or any other sex worker for that matter, had verbally refused was severe. And that was on purpose. No one was allowed to get away with that kind of behavior.

Alanna shook her head and refocused on what was happening. The man had gotten quite hard from her grinding, despite being distracted, and would need some extra care soon. Meanwhile, across from her, Lyra had begun a high energy hand job. This told Alanna everything that she needed to know.

For one, the technique was all wrong. Lyra moved quickly, eagerly. At that pace you could overstimulate and distract the customer. Second, once he came, she had little in the way of cleanup. No one liked washing cum out of underclothes. And finally, she was at a strange angle. People enjoyed being able to return the favor while being jerked off. Instead, the poorer man just slipped his hand down the front of Lyra's dress.

"Excuse me." Alanna interjected. She kept her voice just a little too quiet to be heard without paying attention, but not so quiet that no one could hear it. Another good trick. Both men, and the newcomer Lyra, focused on Alanna. Though her peer did not stop moving her hand, which was a good instinct.

"Oh. I'm sorry. Did you need something?" The richer man asked. She straightened up a little.

"I'm going to the House of Yates. It should be just beside King Maker's Square. Could either of you gentleman bring me there? It would be greatly appreciated." She explained. Lyra's eyes widened. A smile grew across her face as she bounced up and down a little.

"That's where I'm going too!" Lyra chirped. Her eyes grew even wider for a moment as the man she was touching came. She giggled, it was a full-bodied sound that was part innocent and part satisfied but all alluring. Another realization dawned on Alanna: this girl was not all that intelligent. Kind, perhaps, and eager, but not smart. That was fine.

"I see," managed the poorer man, who was still half in a daze. He flashed the richer man a desperate look, one that Alanna could read like a book. It was the look of a man who needed to fuck, or he would explode.

"Unfortunately," the rich man began as he attempted to pull down his pants, "We'll have to take a somewhat longer route than usual." As his somewhat girthy and not at all unpleasant cock was released, Alanna rolled her eyes. It was cute that he was so desperate, but the ploy was just a touch too obvious. She repositioned herself to be facing the richer man, straddling him while positioning herself just above the tip of his cock.

With one hand she moved her underwear to the side, then locked eyes with the richer man. He was sweating, desperate, and very horny. Good. Maybe he would finish quickly. From behind, she could hear Lyra's squeaky gasps as she was pounded mercilessly by the poorer man. Whatever they were doing, it was working for everyone involved.

For Alanna, it was nice to know that someone was still able to provide a nice, hard fuck. Then, there was the matter of making this richer man sweat over something. Most nobles enjoyed this treatment very much. Not just because they were used to getting whatever they wanted, but also that women threw themselves at money. Alanna did have sex for money, but she knew that the sex would come first. With women that threw themselves at rich men, it was often the money on their mind first.

Regardless. She impaled herself on his cock. Then, with strong, confident thrusts, she began to work him. His eyes closed almost right away as a gasp escaped from his lips. Out of instinct, he slipped his hands around her waist and began to shove her downwards. Not only did this turn her on, but it also began to build her orgasm.

The sensation always started in the pit of her stomach. A warm, bubbly feeling that reminded her that sex was designed to be explosive. As she began to pick up the pace a bit, he regained control of his senses. As a result, he managed to kiss Alanna on the neck.

To her surprise these kisses were gentle, but hungry. They were planted just above her collarbone, then traveled up to her jawline. Her orgasm was at her chest now. Which was when he pulled the top of her dress down. It was her turn to gasp now. That surprise must've shown on her face as the richer man smiled for just a moment. With almost animal-like desperation, he began to work on her breasts.

With practiced savagry the richer man began to bite on her left nipple. This sent a shock of pleasure and pain up her spine. That was good, and she signaled that by gripping the back of the richer man's head and rode him even harder. Together, the two of them began to reach the point when their minds went blank.

As Alanna let herself pass over this threshold, she attempted to give one last look at what Lyra was doing. In the corner of her eye, she could see the blonde was pressed up against the door as the poorer man drilled her ass. She was grinding her ass against his cock while moaning like a cat in heat.

That observation was one of the last things that Alanna managed to think after she'd crossed into the realm of just fucking. The next few moments, or they could have been hours, were focused on attempting to ride this cock as hard and as fast as she could while pushing it as deep into her pussy as humanly possible.

Nothing was quite like the orgasm as it ripped through her body. And as it did, she slammed her palms on the wall of the carriage to plant the rich man's dick inside of her just one last time. Despite her best efforts, she also let loose one good moan in pleasure. The sound came from the depths of her desire, and was purely for the sake of letting as many people around her know just how good this fuck had been.

And as the carriage began to come to a stop, she felt particularly generous. In that generous nature, she leaned in to whisper into the richer man's ear.

"Thank you." She said, and low enough that no one but him could hear it. Once he was a little more lucid, this would stick in his mind. Just those two words were enough to give him a story to boast about for the rest of his life. With one last kiss on his cheek, she climbed off, pulled up her top, and stepped out of the carriage.

It took another moment for Lyra too stumble out. When she did, she looked as if she'd just had aggressive sex in a carriage. She was grinning from ear to ear and had forgotten to adjust any of her clothing. With a sigh, Alanna held her hand up to prevent Lyra from going inside.

"What? Huh? Did I do something wrong?" Lyra asked. Alanna smoothed down some of Lyra's hair and adjusted her clothing just a bit. Though she knew that no amount of adjustment would fix how the younger Courtesan looked, but that could work. Some people liked that.

"Just fixing you up a little. And hey, listen." Alanna pinched the sides of Lyra's face, who squirmed, but did not break away. "We're going to go in there together, but I want you to follow what I do. Okay? You don't want to burn out or get into an uncomfortable situation."

Lyra was entirely focused and nodded. It was cute. And to reward her new student, Alanna brushed the girl's hair behind her ear. "You're very cute." She observed. "Would you like me to teach you?" The girl blushed, then gave a small nod.

Without hesitation, Alanna sealed the mentorship the way her Courtesan mentor had done it, a deep kiss. Not just any kiss, a tender, gentle and loving action. Something that so many would not experience because they were too scared of their own passions or would simply prefer not to be vulnerable. And as Lyra melted into Alanna's arms, the two women shared a genuinely tender moment.

When they broke apart, Lyra had a fire lit behind her eyes. Alanna would have preferred a bit more of a screening process for a student, but it was too late for that now. Instead, she offered her arm to Lyra, and they walked up to the front doors together.