Feminine desires

The journey had been an exciting one so far, Kat Jane hinting at a big surprise coming for some time now, though her taunts were becoming much more frequent, Iain sensing it being not long away now.

“So come on, what is it?!”

Katy only giggled to herself in response, almost rolling her eyes as she looked over at him squirming in the back seat.

“You’ll find out soon, don’t worry~”

She almost cut herself off, apparently lost in thought, the driveway was already coming into view. Not wanting to give it away until the last moment, Katy stayed silent until they had pulled in, Iain practically leaning over the seat in front of him to find out what was going on. Though before he could get an answer from Katy, he received it from somewhere else.

“He’s all yours~”

Looking outside the window, Iain was only given a brief glimpse of the women flinging the car door open before he felt himself forcibly pulled from inside, Katy flashing him a smile.

“Have fun now~!”

One of the other women closed the door, letting Katy drive away, leaving him there alone as they already began stripping him down. Trying his best to fight against them, Iain was too weak to stop their assault, feeling the overwhelming sense of dread as the two women tore at his clothes, leaving them as scraps on the ground. After a few moments of struggling, Iain was left there naked at the foot of the university steps, staring up at two snickering women.

While in the midst of their struggle, Iain felt a sense of helplessness, subjected to whatever these gorgeous women wanted with him, he couldn’t help but get an erection from their little scuffle, which they both seemed to find very amusing.

“Awh, look at it~”

One of them leaned down, giving Iain an eyeful of her cleavage as she flicked his tip, eliciting a shrill squeal from his lips.

“Oh my~ this one’s a little sensitive…”

She straightened herself out again, flashing a glance at the other woman, both of them seeming to have come to some silent agreement. Without a word to him, they each took an arm, dragging him through the doors and down the hall as he continued to kick and put up a fuss, not quite knowing where he was yet. Though he was soon to find out, passing by one of the doors that was left open, Iain heard rhythmic slapping coming from inside, catching a brief glance of a woman bent over a table, getting her tight hole ravaged by a woman wearing a strapon… Except that wasn’t quite it. Before he was dragged further, Iain caught a glimpse of a bulge beneath the woman’s panties, noticing a thick, white stream trickling onto the floor…

Iain was frozen in thought, a heat spread across his body as his pent-up fantasy was inches away from him, being played out on somebody much luckier than him… or so he thought.

“Alright, come on now, legs up!”

Snapping back to his senses, Iain looked around to find himself in a rather clean looking room, his body tossed into a white chair with odd straps either side of it. It seemed as though the women were waiting for something, but decided to take care of it themselves, greedily grabbing at Iain’s body, lifting his legs up and above his head, locking his ankles in the restraints beside him.

“There we go~! Now, call her in…”

That faint threat had a sense of fear looming over Iain, not sure what was to come, yet he couldn’t manage the willpower to let his cock soften, the image of that sissy being pegged only a few feet away still in his mind. However, something entirely new overtook his thoughts as Iain witness an effeminate-looking man crawl into the room on all-fours, a drunk look of arousal on his face as he came closer, Iain suddenly painfully aware of how naked he was, as well as how painfully hard he still was.

Without giving him more than a few moments to think, the sissy lunged forward, completely throating Iain’s cock, sending overwhelming jolts of pleasure across his body as the women praised their sissy toy.

“Good girl! Keep going~”

They didn’t need to encourage the sissy much, Iain already on the edge of orgasm, he only lasted a few more moments before filling the sissy’s mouth, letting out a pitiful squeal as the humiliating sensation of being forced to orgasm by a sissy boy washed over him.

Before he could get used to the feeling of having his cock pleasured by a sissy toy, it was stripped away from him, one of the women yanking the sissy’s hair back, a loud pop echoing in the room as his cock was left in the open. Left panting and struggling to steady his breathing after such an intense orgasm, Iain didn’t realize what the women were up to until it was too late, both of them intently staring at his rapidly-stiffening cock, waiting for the perfect time to strike…

Click!

The sound made Iain’s heart drop, a single instant of struggling leading to this… a tight pink cage secured around his cock, a pretty prison to keep him from getting hard… 

Without thinking, he experimented with stimulating himself, trying desperately to jerk himself off and regain some of the mind-blowing pleasure he experienced moments ago. The women instantly snapped at him, ordering him to stop, but Iain pathetically continued to steal away some pleasure, right up until the moment he felt his hands swatted at.

Before he was able to protest to any of his wrongdoings, Iain was roughly pulled from his restraints, tossed to the floor, and then pulled down the halls, trailing whimpers and pathetic begging as he went. He knew that he had messed up as they carelessly dragged him into another room, but the urges were still burning in his chest, even now he didn’t regret getting every drop he could.

After being tossed into the new room, the other woman left, likely to deal with their new student, leaving the two of them alone.

“You know you fucked up, right? Let’s not pretend~”

Iain couldn’t speak, instead he only sheepishly crept backwards, trying to create as much distance between them as he could, but it was futile. The woman took a moment to enjoy the sight of him cowering before turning away, unlocking a nearby draw and then peering through it for something. It didn’t take long for her to happily pull out a toy in her hand… a pink paddle…

Iain instinctively tensed up after seeing it, dreading the sting that was soon to come. The woman didn’t leave him waiting in fear for very long, grabbing a handful of his hair and dragging him over to a chair, sitting on it daintily before pulling him up and over her knee.

“Now now, it’s time for your punishment…”

In such a humiliating position, bent over this woman’s knee, Iain let out a faint whimper of defeat, which gave way to a pained squeal as the first swat of the paddle cracked across his ass. He squirmed and writhed in her grip each time she swatted at his cheeks, his eyes tearing up from the gradual increase in pain he felt with each one, his cheeks becoming so red that even the brush of air began to sting him. This continued for longer than Iain could keep track of, descending into a pit of regret over what he did, every swat became more and more regret, realizing it hadn’t been worth it in the slightest, wishing he could take it back…

Lost in a haze of both pain and pleasure, Iain was rudely snapped back to his senses as one of the other women barged into the room, but he was unable to crane his head up to look at her, only faintly registering their conversation.

“Time’s up, he’s mine now~!”

A faint glimmer of relief washed over Iain upon hearing those words, hopefully finally that he would be allowed to rest and recover somewhat, at least to get used to his new surroundings. Only that wasn’t quite what the stern looking woman had in mind, a sadistic grin on her face as she tagged-out with his previous punisher. Now alone with her, the room somehow seemed deafeningly quiet, Iain waiting for the first hint as to what she had planned for him.

Though he received his answer without a word, the woman shifting in place, Iain saw something swinging between her legs… a thick, black, bitch-breaker of a strapon hung between her thighs, causing Iain to tremble just from looking at it!

Iain couldn’t even find the strength to crawl away, meekly waiting as the woman came closer, making every step painfully slow, right up until he felt her lift him into the air. She took her place in the same chair that he was spanked on, slowly lowering his petite body onto her strapon, savoring the initial squeals as he felt his hole stretched around it.

“Oh come on! We have much bigger for you to train with~”

She worded it in a way that seemed reassuring, but they both knew it was a taunt, letting Iain know how fucked he was, as if the burning pain between his cheeks wasn’t enough. Not wanting him to get too used to things, she began forcing it deeper, pushing him down onto her shaft, feeling his body tremble to the point that he couldn’t even form words to beg for mercy…

Without a chance to object, Iain was left to adjust to her relentless fucking of his tight hole, a slow rhythmic grinding turning into her bouncing him on her lap, but his hole still unable to take every inch for her. While it was a far cry from what he witnessed while being dragged across the hall, Iain felt his lust build slowly, feeling his place as a sissy toy become more attractive, even to the point that he found himself moaning under his breath, letting his eyes flutter shut as he began enjoying the motions.

Still in his training session, the woman bouncing Iain on her strapon decided that a little extra humiliation was in order, as well as a small secret needing to be revealed. With a tug of his hair, she forced him to look up at what his dazed mind either wasn’t able to notice earlier, or she was simply hiding from him.

“Say hi~”

Iain was staring at the screen of a phone, Katy on the other end, smiling over at him. Despite her knowing that this is what he wanted, it was still humiliating to have her seeing him in such a perverse predicament. As if to make things worse for him, the woman didn’t stop forcing him to ride her strapon as he spoke with Katy, causing his voice to tremble with each motion.

Through his whimpers and moans, Iain also caught a glimpse of what Katy was scrolling through in front of her. Tapping away at her laptop, Katy jumped between a few photos and even a video of Iain’s short time with the other sissy… all of these little moments during his brief time at the Sissy University put on display…

Katy didn’t even try to hide her excitement, eagerly looking back at Iain with a wide grin, a cutesy tone to her voice as she spoke.

“Awh, is he coming along nicely?”

Almost as if commanded to, Iain felt his body finally cave to the woman’s constant teasing, letting up for just long enough that she was able to kick his feet out from under him. With his leverage gone, Iain let out a defeated squeal as he slid down her strapon, feeling it press against his prostate, a silent order to put on a show for both of the ladies…

Katy gasped as she watched Iain spurt his cum out from his caged cock, his hips jolting with the overwhelming amount of pleasure coursing through his body, the first anal orgasm of his university stay taking place before her eyes.

“Hm, looks like there’s still a ways to go~”

Her taunting words only made the orgasm more humiliating, feeling his cum pathetically squirt from his caged tip, flinging across his face each time his body spasmed involuntarily, painting him with the proof of his new level of submission. As his orgasm finally died down, Iain realized that Katy had already hung up, leaving him alone with the woman he was idly grinding against, shivering with arousal at the thought of so much more of his training to come…