Working Up to It

Story by serafino on SoFurry

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#7 of As Did the Ancients

Thales has a lot of work to do under his new instructor's watchful eye! But what does a courtesan-in-training get up to when there's no instructor watching? Well, sharing the joy, of course! A shorter one, in preparation for something a little bigger coming after--a plug, if you will.

More love for M/M relations, and specifically the joy of helping someone else learn what they are into.


Like an athlete at the gymnasium, Thales was given a strict training regimen. He awoke and rinsed himself off, before cleaning his interior in the manner Akhnute instructed, and then the lion helped him slip his trainer plug inside him, where it would remain for several hours at a time. At first, Akhnute let him be penetrated in the private room off the main harem chambers, but after a few days he was made to slip it inside himself in full view of everyone.

"Shame is a luxury no longer afforded to you, fox," Akhnute had said gravely as he stood, arms crossed, and waited for the fox to skewer himself while Vespasia looked on with a cruel smirk.

He need not have worried; if Thales was inclined to feel much shame about his anal training, it was quickly abated by the sheer nonchalance of everyone around him. The rest of the harem, he found, was polite but distant. He was still only a provisional member, after all, and he suspected that several did not think he would last. Even Almene barely interacted with him, giving him a warm smile but not engaging much in conversation, no doubt waiting for the emperor's signal that the new boy was one of them for real. Only Vespasia was at all personable, jovially chatting with him and eyeing him up while carefully avoiding saying out loud that she was interested. He enjoyed the conversation with her, strange as it was at first to talk to her about the news of the day while trying to shove a plug up his ass.

His efforts in that department were fruitful, at least. By the end of a week, Akhnute no longer had to help him, and a few days later Thales could comfortably take a canid dildo almost the size of the emperor's endowment, knot and all, and he even got hard when he put it in.

Once he had his trainer in, his morning was spent on light physical exercise, with Akhnute gently guiding him through stretches and flexibility training in the courtyard as the sun began to peek over the roof. Some days, he would train in his new red garments; others, in the nude. When his instructor was satisfied, Thales was permitted to remove the training dildo for the day, and eat a light morning meal before being given the midday to himself. The emperor's summer residence had a small library, a monumental luxury, through which Thales spent hours pacing, reciting and memorizing new poems and songs with which to entertain his new master when the time came. The other courtesans sometimes made use of it as well; they shook their heads in amusement when they found him in there so religiously, but he did not mind. As he had hoped, the emperor had all manner of weighty treatises and plays on hand, and Thales had no responsibilities to distract him from them anymore. He often napped there when the heat overwhelmed him, wiling away the hot part of the day until the sun fell behind the mountains and Akhnute fetched him back to the harem chambers for intimacy training.

Despite the name, what Akhnute called intimacy training was to Thales' mind more like teasing. The fox was ordered to strip, and then had to stand perfectly still, eyes straight ahead, and force himself to become erect with just his mind.

"Breathe deeply and feel the sensation of your balls hanging beneath you, how they rise and fall with your breath. Feel your cock and how it pulses with life, and let that life swell," Akhnute always instructed, and Thales struggled to do as he was told. "You will feel your body react if you relax and focus." Once the fox had done so, then he had to make himself go soft again, then hard once more, all without so much as twitching. It was a strange form of torture, Thales found, all this focus on his arousal with no ability to act on it. Afterwards, Akhnute would instruct him to put in his trainer again, where it would stay until he was ready to sleep.

Thales quickly grew inured to the strangeness of this new schedule. The most difficult part of the whole experience was the emperor's personal guard, always just out of the way, armed and staring after him, a reminder that he was not yet trusted. Their yellow eyes glowered at him from the shadows of the peristyle at all times of day, and what felt like a whole battalion would swarm the area whenever the emperor was about to pass through. They snickered like pups whenever they saw Thales nude in the courtyard, the stump of a training plug sticking out from under his tail, Akhnute scowling at him and softly demanding he learn to ignore their chatter. Of the group, only Asellio was any comfort, his mournful gaze and hesitant grin a source of reassurance whenever Thales returned to the chambers. Unlike the harem, their lupine guardian was not so disciplined about keeping his distance, seeming to see the courtesan todd as a kind of kindred spirit.

"Sore today?" the nutmeg-colored wolf asked in conspiratorial tones one night. Akhnute had left for the evening, and most of the harem was out still, dancing for the emperor and his guests. "You're using the full-sized ones now, aren't you?"

Thales shook his head triumphantly and smiled as he went and grabbed the one in question. "This pup hardly even stings anymore," he said, waving it nonchalantly at the guard, who grinned back.

"I can't believe it," Asellio replied as Thales turned around and placed a leg on a short stool.

Thales just chuckled. "Honestly, the size is only a problem because getting the angle right to put it inside me is starting to be difficult. I'll have to just sit on the larger ones."

Asellio cleared his throat suddenly, making Thales startle and look back at him. The nutmeg wolf's eyes were pinned to his caligae. After a long moment, Asellio looked up again, and Thales saw that the wolf's tunic was slightly tented. With a chuckle, Thales bent over further as raised his tail high, spreading his legs further as he worked the dildo inside him far more slowly than necessary as Asellio's bulge got progressively more and more pointed.

"There," Thales said with finality as the knot bumped up against his ring. "Now only the knot is left."

"I cannot believe you can fit all that inside you," the wolf said.

"It's easy," Thales said, taking a deep breath and popping the knot past his ring. Fireworks shot behind his eyes and he took a moment to steady himself as he knees grew weak for a moment. It passed soon enough, though. "See?"

Asellio gave an exasperated sigh. "Yes, I saw perfectly, thank you."

Thales turned around and gestured at the wolf's bulge with a laugh. "You don't sound quite pleased enough with me for how hard you are, Asellio." When the wolf sighed and looked away, Thales cocked his head quizzically. "Something wrong? You aren't your usual perky self."

"Really? I seem awfully perky to me," Asellio said sarcastically, gesturing at his tented tunic with annoyance. "I think perky is my usual state at this point."

Thales just laughed. "I like that about you. This would be much more awkward to do in front of you if you didn't get so enthusiastic about it."

The wolf's hackles visibly lowered. "Well, I'm glad you don't mind," he said quietly.

Thales made a dismissive noise. "I thought how things went with Vespasia my first day made it clear enough. Not to mention the fact that I am part of a male wolf's harem, for the gods' sake. As Vespasia likes to say, if I didn't enjoy it, I'd be miserable all the time."

Asellio grinned sheepishly. "Okay, okay, I get it, you don't have to bring that up." The wolf's gaze drifted off as he shifted his stance and put a paw gently under his tunic. "You two were pretty hot, though."

"Have you ever done that for the emperor?"

Asellio shook his head violently. "No, no, of course not. I just watch him from the doorway, or from the side of his bed. I don't know why I did it to you, for that matter. Just to play along, I guess."

Thales just nodded, suppressing a small smile. "It was a great time. I hope once training's over, Vespasia and I can give you another show." Asellio nodded and Thales continued, "Or maybe the emperor and I can show off sometime."

Asellio shook his head in disbelief, a sly grin on his muzzle. "Still amazes me that that doesn't hurt."

"It can if you aren't relaxed, but otherwise, no."

"Then what does it feel like?"

Thales stopped and thought for a moment, flexing his butt to feel the dildo he still had inside him better. "Full, mostly. The pleasure is a sort of dull, throbbing pulse when it grinds against your insides the right way." Thales stared into Asellio's face, watching his eyes as he gently continued. "You know, nobody is here. I could show you, if you like."

"No, no!" Asellio said, shaking his head and pulling his paw off his cock and looking out down the hall, as if afraid to be overheard. "I was just curious."

Thales nodded noncommittally and grabbed the smallest plug from where it was stored. He rolled it around in his palm. A most unfortunate servant was responsible for keeping all the harem toys washed. "Sure. I just meant that if you really wanted to know, while nobody was here to see would be the ideal time."

"You wouldn't tell?" Asellio said, still looking down the hall, one paw on the doorframe as he leaned out.

Thales chuckled and walked up behind him. "Of course not!"

"Not even Vespasia?"

"Especially not Vespasia. She's too much of a gossip."

The wolf was silent for a long time. Thales stood there, watching Asellio's tail sway slowly as he peered into the hallway, the distant strains of lyre and kithara wafting in on the warm summer air. It was the deep blue of near-night, when the sun had gone but its light still arced over the horizon and turned the sky indigo. The hallway itself was only lit by ambient light, and at this time of night the white marble shone eerily in the darkness, cold and bluish.

"Afro just turned the corner. Do it now," the wolf said suddenly, bending forward a little further and lifting his tail high. Thales couldn't help but laugh softly as he licked over the plug to lubricate it and then held it gently against the brown wolf's hole.

"You'll need to relax so it will go in, Asellio," the fox said, and the wolf spread his legs a little further apart and sighed audibly. Feeling mischievous, Thales reached down with the other paw and rubbed Asellio's furred sack between his fingers. It was drawn tight against the groin in fear or excitement, and Asellio moaned audibly as Thales massaged it. Above, his tail began to gently wave, and Thales felt the hole start to give way as he pressed.

"It's in," Thales said at last, though he needn't have; the wolf's loud, delighted cry made it clear that Asellio had noticed already. He stood that way for another long moment, frozen except for his tail, which waved furiously above him.

"Is that all of it?" the wolf finally asked, and Thales' eyes widened with surprise and amusement.

"Yes, I gave you the smallest one. Do you want a bigger one?"

"Hurry," Asellio replied weakly. "Their patrol route should be back here soon."

Thales went back and grabbed a small dildo, four inches long and almost an inch thick. When he returned, the wolf was wagging so manically that Thales had to grab his tail so that he could get close enough to switch the toys out. The plug was removed easily, and Thales quickly brought the new dildo up and slid it home to an ecstatic sigh from Asellio.

"Better?" Thales asked sarcastically as the wolf straightened up and turned around gingerly. In the dark, Thales could just make out a damp stain above the bottom hem of the wolf's tunic, rapidly growing larger as the guard's erection continued to gush pre. Thales smiled with satisfaction.

"It was easier than I expected," the guard said. "I was expecting it to hurt more."

"You were very relaxed," Thales said approvingly. "I wish I had been so relaxed my first time."

"You found it more difficult?"

Thales nodded. "Now I'm fine, but it took me a day or two to get to what you just took. At this rate you'll be ready for the real thing before me."

Asellio's breath caught, and there was a long, awkward silence as the two of them stared at each other, twin rods standing out from their bodies, straining toward each other. "This was just to satisfy my curiosity," the wolf finally said, looking down at Thales' member. "I'm not trying to get with a member of the emperor's harem, you understand."

"Of course," Thales grinned triumphantly, as bubbling laughter suddenly ricocheted down the hall.

"That sounds like Macula and Ambusta back from entertaining," Asellio said, straightening up and returning the door as he tried vainly to hide his erection. "And it would seem they brought the emperor back with them."

"Do you want me to take it out?"

"No, no," the wolf waved him off. "No time. I'll leave it in."

Thales grinned. "If you'd like."

"Shut it," Asellio said, though Thales could hear the small grin in his voice. "You've got a bigger one in you."

Thales laughed as the commotion drew closer and went to lay on one of the couches, as though he had been roused just now from sleep. "Eh, you'll get there soon enough."