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Well, this was it. Standing before the door to Circe's office, Jean took a small moment to compose himself. This whole business had started only a few weeks ago, when he realized how much interest he was starting to take in some very feminine clothes. Some quite impure thoughts had come with, which eventually led him to seek outside help when they didn't go away. Circe was a rather intimidating woman, but she proved very understanding of how he felt. It was hard not to feel a little ashamed of something so taboo, but she never tried to ridicule him for his fantasies. In fact, she encouraged him to try to explore his feelings, see if how much he enjoyed it in reality.

First, she suggested he buy some woman's underwear, wear it around for a week. When he responded very positively to the experience... why not take it to the next step? Find some nice girl's clothes and embrace his fantasy fully until they next met. Buying it had been a rather awkward experience, and there was that little twinge of shame wearing it in public... but it felt good. Jean wasn't of particularly masculine build, but just a feminine top, a skirt, and some stockings held a much more transformative effect than he had really expected. He'd even been called "Ma'am" a few times!

It had been a thrilling, if somewhat intense, week, and it led him once more to the owl's door. The rabbit girl at the reception desk had given him a very knowing look as he rung up to let Circe know he was here, which only seemed to heighten things. She said last time that, if he wore the clothes to their session, he would be ready for a much more intensive next step. He didn't know for certain what that meant, but he was sure the he could handle it! Taking a long, deep breath... he opened the door.

Stepping into Circe's office with the door, he realized instantly that he was not prepared for what was on the other side. The imposing owl stood to the side of her desk, which had been cleared and used instead to surface a number of very lewd implements... and she was almost completely nude. Only a pair of black lace panties gave her any coverage whatsoever. Her large chest and many curves were exposed to the air entirely, and the large shape within her singular covering suggested... oh wow. "Jean, just on time as usual." she said, as exquisitely composed as always despite her nudity, "Close the door, would you?"

Uncharacteristically speechless and blushing fiercely, Jean simply nodded and did as instructed, shutting the heavy wood behind him with a quiet thump and click. "I apologize for the surprise, but it was the only way to be certain." Circe continued, drawing slowly nearer, "It is my experience that crossdressing fantasies in boys such as yourself, who aren't truly wishing to become a girl, almost always come with a number of... other desires. You likely aren't fully aware of them, but your reaction just now spoke volumes. You immediately centered on me, and on my crotch. Modesty demands you look away, and you're embarrassed by that, but you can't pull your eyes away, can you?"

She was quite close now.

"You are a virgin, yes? Or very close to it?"

A small nod was all he could manage, still profoundly flustered.

"You have... experimented? Fingering yourself, perhaps edging?"

Another nod.

Now standing right before him, she leaned in close.

"Would you like to know a secret? That rabbit, the one who buzzed you in? He was very much like you during our first sessions." Circe said quietly. Jean's eyes went wide. He? That was a boy? He had been quite certain the rabbit was a girl! "Do you want to experience what he has? I taught him the pleasures that submission can provide, and I can show you, too. It won't be an easy learning process, but I am quite certain you will be happier for it. You've liked everything so far, no?"

With all the emotions the scenario was stirring up, amplified by the owl's own action and proximity, Jean was having trouble responding. Circe was already kind of an intimidating woman, somehow more so in the nude, and the idea of submitting to her was simultaneously very scary and very attractive. But... she was right. All the things she'd encouraged him to try previously had held a similar mix of nervous excitation, and he had enjoyed all of that, hadn't he? After some hesitation, which she seemed quite patient for, he made up his mind. One more tilt of his head, and he finally spoke.

"Yes... ma'am."

That ever-present intensity in her eyes didn't leave, but she seemed to be pleased with his decision. "Good girl." she whispered ever so softly, sending a tingle through his spine as she pulled back slightly. Placing a hand on his arm, the owl guided him away from the door and brought him instead to the desk. "Sit. There are a few things you will need before we start." Circe instructed, helping him rise up onto the emptiest part of the desk's surface.

Closer, and slightly less distracted, he got a better look at what she had laid out on it. A sizable purple dildo, and the plug beside it, was the most eye-catching, next to which was what could only be a collar, alongside which was... something. It looked like a tiny cage of some kind, with a concerningly phallic shape. He could certainly guess at what it was, but surely she wasn't planning on...?

His reverie was broken as she stepped over to the assembled items, grabbing the collar, plug, a small bottle of lube, and the metal thing to place beside him. The collar was her first focus. "If you want to submit to another, I find physical reminders are very useful. Helps keep... focus." she told him, wrapping the leather around his neck. Pulling it closed and latched, it was tight enough to be felt without restricting airflow. It would be hard to completely forget about, he suspected. Her focus was already shifting downwards, however, to his skirt. She wasted little time hiking it up, exposing the soft feathers of his uncovered thighs alongside the snug black panties he had bought. He couldn't help but jump slightly as she touched those, but made no protest as she started to pull them off.

Soon, that most private area was truly uncovered, exposing his growing arousal. Just from what he guessed was going to be the tamest part of this, he was nearly at half-mast. "Hm, that's inconvenient, but I suppose it's to be expected." she said, seemingly mostly to herself. Without much in way of warning, a taloned hand reached forward and took a grip of his partially erect member! A small, rather uncharacteristic gasp escaped Jean's throat at the touch, but she certainly wasn't done. With a quick, rather merciless sort of efficiency, she began to stroke. Her goal was, quite plainly, to get him off as immediately as possible... and it was certainly working, especially with how aroused he already was. Within a minute, his breath was heavy and grip on the desk's edge tight as that climax grew near. Just as he starting to twitch in her fingers, however, she suddenly stopped, wrapping her thumb and forefinger tightly around the base of his cock. Powerful as it was building to be, the shift left it a very weak orgasm, completely dry thanks to her vice around his shaft... but it was enough to make him begin to soften.

As soon as he was fully limp once more, she brought the metal back around. First was a simple ring with a small piece at the top of it. She slid it down to the base of his length and, with a bit of effort, slipped his balls through it. After that was the main piece, the cage itself. Compressing his cock slightly, she fitted it down to the ring, holding them together as she retrieved the final component: the lock. Small and made of brass, the quick click as she closed it held a strong sense of finality. He was, truly, in her control now. It was, much like the owl herself, simultaneously a bit frightening and very arousing.

"Good, good. That's much better. You will have no use for this, so it is better to keep it contained." she said, caressing his balls lightly. "Now, turn over for me. I have one more addition before we begin your training." He was quick to obey, stepping down and laying his front across the desk, leaving his behind vulnerable. Where had such a ready obedience come from? So surprised with himself, he was, that he almost missed Circe bring the plug and lube over. "See? You are taking to your role so quickly. Almost no hesitation that time." she praised as she stepped behind him. He heard the sound of the bottle open, and a slightly wet sound he guessed was her spreading it across her fingers. A moment later, he felt talons on his rear, spreading one side open to reveal his nearly untouched pucker. The sensation after elicited a small, surprised yelp from the vulture, not born of her touch to his entrance, but to the coldness of what coated her digits as she did.

Cold as they were, though, those talons had a purpose that he was naught to stop now. Gently, she pressed them in, two fingers, much more rigid than his own, sliding in smoothly with the aid of lube. There was a moment of concern for their sharp ends, but it was clear she was not inexperienced with this in the slightest. She navigated expertly, giving him the slightest sensation of her talon tips without any hint of pain. It was a much stronger experience than his own, very light, experimentations using his own fingers... and she had only just begun.

Slowly, she began to increase the pressure exerted, sinking a little deeper with each passing moment. Her fingers were quite long, and he could feel the way they spread and stretch his unclaimed hole. Much faster than he would have expected, however, a slight bump at his rim made him realize he had taken them entirely! Perhaps she was right about how natural this was for him, he thought, only to be shaken as she started to pull back. But Circe had no plans to exit just yet, suddenly pushing back in right instead of leaving him empty once more. The cage felt much tighter than it had mere moments ago, a realization that was amplified massively as her fingers grazed a very sensitive spot indeed.

He couldn't help but gasp a little, but in doing so, he told her exactly what she had just done. It was information the owl was quick to capitalize on, immediately shifting her angle to stimulate his prostate with each press inwards. The constant sensation made him squirm, unprepared for how strong it really was. He could even feel precum leaking out of his cage, but the constant pressure of his blocked erection was ever-present. That continued on for a short while longer, Jean never really approaching orgasm despite the stimulation, before she finally pulled her fingers free with a quiet popping sound.

His reprieve was very short-lived, however, as another, larger object was brought to his behind. He knew immediately it must have been the plug, coated in extra lube, that was pressing against his entrance. It took considerably more work on Circe's part, but he could feel her slowly working the silicone toy deeper, bulbous shape stretching his insides to a much greater degree. The excess of lubricant kept it from hurting as it might have otherwise, leaving him with only that pleasant sensation of being spread. Finally, with a sudden lessening of tension, the last of its length was buried inside him, resting right against his prostate. It was an incredible feeling, being so full, and the now-constant press against his most sensitive place only made his caged length leak more.

With that finished, for now, Circe was eager to move on. First, she removed the skirt entirely, pulling it off him and tossing it aside before helping him stand again. "You already know how to dress like a woman, but if you want to truly sell it you need to move like one, too." she told him, "I want you to walk across the room a few times for me. While you do, try to let your hips swing out more, add some bounce into each step. The plug should help."

It... wasn't exactly what Jean had been expecting, but he had little desire to disobey now. So, with some degree of uncertainty, he began to slowly pace back and forth in front of her desk. Each step caused the plug in his rear to shift considerably, rubbing against his prostate. It made it a little hard to focus, but the stimulation actually did seem to push him towards a way of walking like what Circe wanted. She stood to the side, observing quietly, as difficult to read as always. "Cross over when you step more." she advised, "You want your behind to bounce while you walk."

Eventually, she raised a hand from to stop. "Good...yes, very good. You are quite a natural at this, Jean." Circe praised, gesturing for him to approach. As he did, a small glance back caused him to realize he had been... dripping. Oops. "You will need more practice, of course, but it is a very promising start." the owl continued, "Next, you will need to learn how to serve another, if you wish to take this role seriously. Down." With that final, commanding word, she pointed a single talon at the floor. Almost immediately, to his own surprise, Jean found himself on his knees before the therapist, right on the level with her dripping member.

"While you cannot perform here in quite the same way as a non-avian could, oral is still an excellent way to show your appreciation for your partner. Use your tongue and your hands. Show me how very grateful you are that I am training you." Circe ordered, tone growing noticeably more assertive. As before, he was quite quick to comply, leaning forward to gently place his beak against her balls. Resting right against the base of her cock, he was immersing his quite strong sense of smell in the scent of very strong arousal and sweat. It seemed everything so far had done much more to excite the owl than she showed obviously... and he kind of loved it.

It was a very naughty sort of musk, absolutely bathed in her own arousal and amplified by how warm her body was to the touch. He wouldn't have needed any instruction for his tongue, as it snaked out by its own volition to taste it directly. Yet, even as it ran along collecting the taste of her salty sack... his hands were not idle. Almost on instinct, they reached up above, gripping her impressive length and beginning to stroke. Slowly at first, but quickly he gained speed. It felt incredibly overwhelming, burying himself in her like this, but it was simultaneously _intoxicating._From the way her breathing changed above, and he felt her perspire more, it was clear how much Circe was enjoying it too... but it was not to last.

In order, he suspected, to prevent either of them from getting carried away, she eventually pulled him away. As she helped him stand again, he found himself muttering a quiet "Thank you." When he did come face-to-face with her again, however, he realized how much her composure had crumbled from such a short interaction. Lust was written across her features, and with it a hunger that was both incredibly enticing... and kind of scary. With surprising strength, she pulled him in hard, burying his face in her chest. "I was going to take this slower... but you are truly made for this, Jean." she told him breathily.

Without another word, she turned the vulture around quickly, facing him to the desk and bending him back over it. A moment later, he felt a slight tugging as she pulled the plug out of him with a quiet pop. Though he kept his head down against the desk, the sound of a lid clicking open and the wet sounds following told him all he needed to know. Indeed, he was proven quite correct as something much warmer than a sex toy pressed against his rear. Both of her hands gripped firmly his behind, spreading his cheeks wide as the pressure at his entrance increased. Circe was much thicker than the plug had been, but it was an inexorable force she output. Within moments, aided by the lube and her own insistence, Jean felt his entrance open as her head slipped inside.

His breath caught in his throat as she entered him, unprepared for just how much bigger_she felt inside him. And she was far from done. He was only given a scant few seconds to adjust to the feeling before, as was inevitable, she continued. That pressure returned, and with it, ever so slowly, she pushed deeper as her hands moved to his hips. With every tiny bit of progress, he could feel her stretching his ass out, molding him to her dick... and it felt incredible. The plug had been a constant, shifting tease, but _this was something else entirely. By the time she had buried half her length inside him, Jean could feel his own member straining against the cage again, vying for a freedom that had been denied.

Circe, meanwhile, was finally starting to pull back, but that was only because her progress had stalled. Once she was back to just the head again, a sharp thrust forward sunk her a little deeper than before. It was a process that repeated, each time drawing a quiet little gasp from the boy beneath her... a boy who was quickly learning just how right she had been about him, after all. One thrust, though, seemed to elicit a much stronger response from the vulture, about three quarters her length inside him, and she knew she had found his prostate. Immediately, that became her target as she picked up the pace.

With every impact of his most sensitive place, Jean felt almost as if he was melting. Each thrust seemed to wring out a little bit of his cum, the white fluid leaking from his aching, caged prick more and more. Yet, for as incredible as it all felt, even as she began to bottom out and her sack slapped against his own... Jean couldn't quite_seem to reach his peak. She really was going quite heavy by that point, and he could hear how ragged her breathing was becoming, but orgasm was just barely eluding _him with each thrust.

Soon, the organ hollowing him out began to throb menacingly as Circe's thrusts grew increasingly disorganized. He knew exactly what it meant, but there was little to do now but brace himself for what was coming. Indeed, only moments later, she made one final, hard slam inwards, shocking his breath out of him for a second as her orgasm began. For a short moment, there was only the incessant pulsing of her member, buried completely within him, but then he felt the warmth. It was like a flood of a most incredible heat, spreading through him and into his stomach, all kept inside by just how tightly he clamped down around her. Still, his own peak eluded him... but he didn't really mind in that moment. It felt good, just serving Circe.

They stayed there, panting heavily, for what Jean suspected was only a few minutes but felt like forever in the best way possible. Eventually, though, the owl above him began to move. Slowly, carefully, she extracted herself from his insides, sliding out with a lewd, wet sort of sound. Almost immediately, he felt the plug slide back inside, though. "That was... incredible, Jean." she said, clearly still short of breath, "I think I was more right about you than I entirely realized." Much of her formal demeanor seemed to have slipped from the experience, but she still helped him off the desk. His legs were more than a little shaky, but he managed to stand, at least.

"Unfortunately, I can't keep you here much longer." Circe said, glancing at the clock beside the door, "But I think you can agree we've found the right place for you, yes?" Jean could only manage a small nod in response, but it seemed to please her. She helped him put his panties back on over the plug and cage, as well as his slightly rumpled skirt. "If you come back to me next week with the plug in, I'll make sure there's more of today." she said, placing a hand on his shoulder before leaning in close and dropping her voice, "Perhaps I'll even take that cage off, hmm?" Jean felt his cheeks grow hot as he turned away slightly, but still he managing a small nod.

She pulled him close, pressed right against her body. Her next words were naught but a whisper, dripping with lust...

"Good girl~"