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To say that college was a time for experimentation might be a little bit stereotypical, but for Ronnie, the statement was proving truer than he ever could have imagined.

He was sure that he was going to fail out of his classes for the semester. It was already late spring, but he didn't know if he could make it back home in time to finish his finals, and for some reason, he wasn't reporting Duke to the police, despite the fox essentially keeping him against his will.

Ronnie consented from the start, as his homosexual bout with the vulpine was done in order to learn the secrets of seduction. Naturally, Duke never followed through with such information, being gay, but Ronnie made the foolish mistake of agreeing to follow the fox back to his home city, where he ended up discovering not only that the fox wasn't any kind of a womanizer, but that he preferred to dress like a woman, rather than hit on one.

After an evening walking around in a skirt and tank top himself, Ronnie didn't feel any closer to figuring out the secret of how to get women to fall for him, and worse still, he was starting to enjoy the company of the fox, despite being assured that he was straight his entire life.

Indeed...college was proving to be a bit more of a trial on his mind than he anticipated, and if he didn't make it home soon, this entire trip would prove to be little more than a waste of his time.

"Listen, Duke...this...whatever this has been, this has been a good time and all, but it's been a week. My professors are getting tired of my excuses...I don't think I can put this off any longer. You've got to get me on a plane back home today!"

Ronnie was getting used to the idea of waking up next to Duke, and knew that some kind of groping in the morning was little more than the fox following his own customs, but he still wasn't under the control of the vulpine, just yet. He was still thinking for himself and couldn't shake the fear that he was wasting his tuition money with the trip, no matter how many times Duke assured him that everything would be fine.

Of course, Ronnie wasn't aware of the extent of Duke's intentions, and as the fox rolled over in their bed and gripped Ronnie by his bulge, he wore a devious grin, feeling perhaps a bit too sure of himself, and his plan. "How about I get you back on a plane tomorrow, Ronnie?"

"I'd really rather do it today."

Sighing quietly, Duke shook his head. "Well, I can't possibly afford to get you on a same day flight, and I doubt you've got that kind of money lying around, either. How about you let me treat you to a date tonight for all of your troubles, and tomorrow, you can fly home?"

After being paraded down the streets of a crowded city, wearing a skirt that failed to cover the tight, gripping panties that he was forced to wear, Ronnie couldn't imagine any scenario in which a date with Duke would be anything but a mistake. He was still worried, though, that the fox was his only key to getting home; he couldn't possibly call his parents and ask them for help.

They'd never understand what he'd done.

"I...I guess I've got nothing else going on tonight, in that case," the nervous feline admitted. "But I want to be on a plane tomorrow, and I want you to swear that on your life."

Such a threat might have worried others, but Duke was cocksure that his plan was going to come to fruition, and as far as he was concerned, Ronnie wasn't any kind of a threat, no matter what he said. "Oh, I swear it," Duke replied, not even bothering to cover up the hint of sarcasm upon his tone. "Though, I've got a caveat of my own."

Despite it being against his better judgment, Ronnie let his guard down, actually believing that Duke was going to send him home the next day. It made him much quicker to comply when he foolishly asked, "And what is that, Duke?"

"You've got to wear the same outfit from earlier this week...and I want you to put a plug in your tailhole during the date."

Crossdressing was already awkward for Ronnie the first time, and under the warmth of the covers, he still managed to shiver, not because of the way that Duke rubbed and massaged his cock, but because of the terrible memories of how strange it felt to be dressed that way.

"Duke, I...I c-can't do that. No deal."

"There's a plane ticket with your name on it if you agree to my terms," Duke reminded him. "I'm afraid I can't be flexible about this, though."

It was all a power play by Duke, who was seeing just what levels of depravity he could push Ronnie to. The feline was already in the middle of the strangest week of his life, and his lifestyle, sexual preferences and future had all come into question, in ways that he never believed they would.

Just reflecting on that fact made Duke's request feel a bit more reasonable, and though he was still reluctant, Ronnie gave a quiet nod. "F-Fine," he replied with a shaky voice. "But you'd damn well better come through for me, Duke."

A firm grip took hold of Ronnie's cock and squeezed it. "You've got nothing to worry about, Ronnie...shall we get you all gussied up for your date?"

**

In a larger, metropolitan area, the world had a tendency to be a bit more progressive, and as such, no one was casting a glance at Ronnie and Duke, despite the two of them crossdressing in public at a fancy restaurant.

They were staring at Ronnie because the poor feline couldn't manage to sit still in his seat. The short skirt around his hips was riding up, giving a preview of his panties to anyone who dared to look, but only a privy few were aware of the real reason why he was so uncomfortable.

A few curious, prying eyes were able to see the bulging, disc-shaped end of the plug in his asshole through the thin fabric of his panties, and though he'd been able to take Duke earlier that week, Ronnie was still inexperienced overall when it came to anal play. To keep a plug in took a certain degree of practice and skill that he simply didn't have, and knowing that the base of the toy was stretching out the back of his panties with each step made him overjoyed to finally be able to sit down...

...Until he actually had to sit.

"I know you're still...adjusting to the changes in your life," Duke pointed out, "But you're only going to draw more attention to yourself if you keep bouncing around in your seat like a caffeinated child."

Gritting his fangs and casting a glare at Duke, Ronnie reached out and gripped the edges of the small table, knowing that there were plenty of people gazing at him that didn't have any idea what was going on. "Do you have any idea how difficult it is to sit on one of these things?"

"If you relax, it'll be a lot more enjoyable."

"Easy for you to say," Ronnie shot back as he rolled his eyes. "Someone had to have seen that thing pressing against my panties. I can't believe we haven't been thrown out of here yet!"

For a restaurant that served their drinks in crystal, had floors of fine marble and limestone, and brilliant chandeliers dangling overhead, casting just enough light to create an ambience, the rules didn't seem to be too heavily enforced. Though Ronnie and Duke were dressed convincingly enough to make anyone believe that they were females sporting short headfur, their outfits were revealing at the very least, and though it was hard to blame the feline, he was having quite a bit of trouble keeping his voice down.

The entirety of it created the illusion that Duke had powerful hookups in the city, and Ronnie, in his youthful naivety, bought right into the idea.

"We're a pair of gorgeous ladies, enjoying an exquisite meal together," Duke pointed out. "No one would dare to throw us out, unless we hopped up on the table and started dancing in our own food."

Ronnie was sure that the explanation couldn't be that simple, but as he did his best to slide the toy deeper and deeper into his ass so that he could properly take a seat, he noticed that he no longer felt the gaze of strangers tingling upon his fur. The more settled he became, the less attention he drew, and though the entirety of the situation still felt awkward, that sensation was starting to pass, as well...and he couldn't decide if that was a good thing or not.

"T-this...this is all very nice," Ronnie admitted, though he was nervous to give Duke any credit. He didn't want to give the impression that he was settling in. "Thank you for taking me here."

"It's all part of your training," Duke suggested. "You've got to learn to be patient with a woman, especially if she's a bit jumpy and eccentric."

If anyone actually believed that Ronnie was a female that night, such words would have fit the bill for him. "You could have mentioned that at the beginning, y'know."

"It was more fun for me to watch you squirm around that butt plug."

"Hmmph. I bet it was."

"I'm just being honest," Duke said. "I sincerely doubt that small gesture is going to be enough to ruin the date for you."

Before Ronnie could protest, his drink was refilled, and immediately after, his wine flute was turned up, and he was given a sample of one of the house blends. "Thank you," he replied politely to the waiter, before turning his gaze back to Duke, who was snickering at how easily distracted the feline was. "You're almost too confident about the success of this date, Duke."

"Exactly. I'm almost too confident, and yet," Duke paused, as he lifted his footpaws under the table and rubbed Ronnie's cock through the delicate, silky fabric of his panties, "You're enjoying how sure I am of myself, and the light banter of my company. Just like all of the girls I've ever dated...I'm starting to wonder if you're better off as a female, rather than trying to seduce them, Ronnie."

When it came to Duke and his approach, the mind games were endless. Everything went as planned until this very moment for the crafty vulpine, and the prompt was part of the game, as well: he needed to see how Ronnie would react before he could take the next step.

It was all too common that a typical, college frat male subconsciously considered women to be beneath them, and if Ronnie was still of such a mind, he'd likely lash out at the comparison.

Instead, his face went pensive, and his lips thinned across his muzzle as the idea clearly gave him a lot to think about. Between the surprisingly delicate pawpads rubbing his manhood through his panties, and the wine glass that he held so gently in his pawtips, Ronnie was beside himself with wonder, about if he really would make a better female than a male.

He took a dainty sip of the house blend and set his glass down with a quick wince, as toes curled and brushed around the very tip of his length. Precum was staining against the thin, white cotton as Duke reminded Ronnie that he certainly was male, but the seed of doubt was finally taking root, as Ronnie tried to deny the pleasure that he was feeling.

"If you've been with as many women as you say," Ronnie finally replied, "Then why are you taking such a great interest in me? Why would you bother sleeping with a guy at all, if that was the case?"

"I've got my reasons," Duke immediately shot back, his answer sounding routine and practiced. "You shouldn't worry your pretty little head about it. For now, just understand that I enjoy the challenge...and you're putting up just the right amount of fight to keep me interested."

Whether it was the wine, the teasing touch against his cock, or the fact that he was still in a whirlwind of emotions from such a crazy week, Ronnie just couldn't quite see through Duke's scheme, even when the fox was almost literally putting it on the table in front of him.

He just gritted his fangs and tried not to cum against his panties as Duke masterfully rubbed his footpaws against his cock, stringing him along little by little.