Sasha Sucklove's Sissy School Ch. 06

We're currently a month into Adam's time at Sasha Sucklove's. If you want to read five months ahead, or read any of the exclusive spinoffs and one shots in the Sasha Sucklove's universe, check out my site. And even if you don't, I love all your comments and feedback here! Thanks for reading!

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Relief.

That word seemed like poison here, like some cruel trick or joke. Adam couldn't imagine their overseers actually caring about them, actually wanting to give them any sort of solace or comfort. And after seeing what they'd done to Hannah, what they'd done to Gina...

The worst part, as he now realized, is how apt those names now seemed. He used to find it odd to think about boys with the name Cindy or Sue. Now, he probably would have felt the same way if he thought about them with their original names.

He bet that no one batted an eye when they called him Eve.

"So... what's the plan?" asked Cindy as they sat on their dorm beds.

"Well, that Ethan guy escaped. We need to figure out how..."

"Only there's no way they haven't plugged that hole already."

"Then we find out how they plugged it. We need to gain their trust though. No more trips down below."

"You think I want to go down there?" scoffed Cindy. "Besides, I think you're the only one left who hasn't been down."

Adam grimaced at that. There was no way it was true.

"Whatever the case, we have to find out the escape first. You ask around with the older girls."

"Boys" came Cindy's annoyed correction.

"Right, sorry. Ask them."

"They won't tell. You know them, they're terrified of their own shadows. Their shadows could probably take them in a fight too..." he muttered.

"Well figure it out. I'll keep being the good girl they think I am. I don't care what they do to me, I'm going to do something so they never do this to anyone ever again."

BRRNNNGGGGGGG

Adam sighed as they heard the bell. This was a new class, so there were arrows waiting on the floor for them, leading them on. He couldn't help but look at the long line of girls moving in 6 inch heels as if it were nothing at all, skirts bouncing and swaying, arms moving with prissy little swishes until they reached a hallway filled with doors. Each one had a name. One student for each door.

Adam gave Cindy a look that didn't seem very self assured.

"ENTER" came the voice over the intercom. Guards in their faceless swat gear appeared at the end of the halls as if to make their point clear. Adam slowly reached forward and pulled it open, heading inside as the others did the same.

There was a curtain waiting for him, as white as the rest of the antiseptic space. It was almost glaringly white, and the door shut behind him. A click told him there was no way out until he was let out. And as soon as he was trapped inside...

The curtain parted.

A beautiful blonde walked out, wearing nothing at all. It went to show how messed up Adam's perceptions had become that he immediately compared her to Bri, and found this girl wanting. But that was the thing. She was a girl. She was a cute, naked, cis woman, standing there and looking Adam over with a smile on her face.

"Hi, I'm Ally" she said as she extended a hand. Adam looked to it like it was radioactive. "I'm your relief officer. Here to help your pent up little balls" she explained as she stepped closer.

"Help? Right..." said Adam as though he was waiting for the other shoe to drop.

"Yes. Help" she assured him kindly. "The cages have moisture detectors, you know? And yours has been reading some pretty excessive leakage. Poor thing. You must be so needy" she smiled, her blue eyes looking him up and down.

"So what, you're going to take my cage off?"

"No, that's about the only thing I can't do. But, I can help you in other ways" she smiled, reaching down and lifting his hands onto her bare breasts. "Do you like that?"

"Um... yeah..." he said awkwardly.

"You can touch me however you want. I'm yours for the whole relief session. What do you want to do?" she asked.

"Um... uh..." he thought for a moment. He hadn't expected this. It had thrown him for such a loop that he had absolutely no idea what to do. He just leaned forward, as if on instinct, and started to motorboat her breasts.

"There you go..." she cooed, letting him do whatever he wanted. He reached back to grope her butt, suckled on her nipples, leaned in to kiss her. It had been so long since the idea of being with a girl had even occurred to him and if this place was going to take so much away, they might as well give him this. He deserved something in return. Some solace. Some relief.

His hands moved up and down her body. His lips explored her. He got so worked up as she stood there and accepted everything. Finally, he bucked his hips to grind against her. But that made him stop.

He had nothing to grind with.

"Aww... forgot about that?" she asked, reaching under his skirt and flicking his cage. He blinked for a second. He had let himself get so worked up, so into it, that he forgot that there was no outlet. "Here..." she offered, reaching over and lifting his pink top off. She helped him undress until he was just in his bra and panties. But as soon as he got that naked, he shrunk in shame. He looked like some little bimbo, like some hot girl in lacy lingerie. Ally pouted and reached back, unhooking the bra and taking it off.

Adam wasn't sure what she was doing, but he let her. He was down bad by now, tricked into his own fantasy that had no way to resolve. Ally gave him a soft look and reached forward, putting her hands on his breasts.

"B cups?" she asked as she massaged them. Adam blushed as her expert hands immediately got what she wanted. This was her skill, after all. She was talented and well trained. She knew how to please a sissy. Soon enough she pulled her hands back and tweaked his hard nipples, sending a shiver down his spine and a gasp from his mouth. It was like wild electricity was running up and down his back.

Now Ally leaned in for a kiss, her body pressing against his while the hands did their work. She guided him behind the curtain where there was a bed waiting then guided them both down into it. As her stimulation made him coo and pant, she reached back and took a handful of his pantied cheek. He didn't care. He was in a haze of need, too focused on overwhelmed nerve endings to notice anything else.

His little noises sounded so cute and high pitched.

She continued to tease him like that for a minute or two as he reached a fever pitch, and then snaked her hands into his panties. He didn't stop her, of course. She'd been exploring back there already. But what finally made him take notice was her index finger, slipping between his cheeks and-

"Ahahhhhhh..." he moaned.

"That's good. That's a good boy. You're my man..." she whispered, pressing into his plug before grabbing the key she had hidden in the sheets and taking it out of him. He was stunned, but it had felt so good. It had felt incredible.

Ally smirked as she put two fingers inside of him and pressed them to his sissy button.

"Holy Shit!" he moaned.

She shushed him and cooed into his ear as she did her work, letting him kiss and grope her, letting him do whatever he wanted as she worked his hole. She knew exactly what to touch and exactly how to touch it, rubbing his inflamed little prostate as he leaked into the front of his panties. They were soaked through as she worked him up, soon getting him to the point where he was brazenly moaning like the sissy he was. He was so close, so close to finishing for the first time in a month, to getting relief after the most lewd and teasing month of his entire life.

Then, she pulled her hands away.

"What... what?" he asked, looking to her with betrayal. She grinned.

"I'm only allowed to get you there with that..." she said, pointing to a strapon laid out on the bed stand. Adam gulped. He wasn't going to... that would be insane. He was smarter than that. Stronger.

But he was also sure he'd never needed to cum so bad in his life.

"So, what'll it be?" she asked.

Adam hesitated.

Then, he nodded.

"Good call. Why don't you help me follow proper protocol" she said, taking out bonds from the bottom of the bed for him as she stood up to strap on. "I need you tied down so I can put the plug back in after."

Adam would have done anything then. So he laid there as she reached down and roughly turned him over, surprising him with her strength and his inability to resist it. How weak was he?

Whatever the answer was, he wasn't strong enough for the bonds that now bent him over the bed, knees attached to the floor and body affixed to the mattress. She put some lube on the tip of the strapon and rubbed it up and down, practically making him pant with desire.

"That's my big strong boy..." she smiled, giving him a pat on the butt before lowering his panties. Reaching down, she parted his cheeks and began to slide the thing into her puckered hole. It was strange and cold. The initial sensation was almost enough to make him change his mind, but then it hit his prostate. She rubbed it forward and back before pushing in deeper, getting to the point where Adam's tightness required some extra strength to push it in. He grunted when she finally got the thing inside. "Very good. You've been so good..." she whispered to him before starting to move the thing in and out, making sure to grind it against his sissy button with each buck and gaining strength with each thrust. It felt so good. Maybe it wasn't as good as a real release but he needed it after all this. She started to work him back towards his goal, the strapon warming up inside of him as she cooed.

"You like this?" she asked, pulling out for a moment and then smacking on Adam's booty. "Good. You deserve it..." she said, before he felt the warmth and fullness return. He couldn't see her, but he felt her hands. He heard her words. He felt her thrusting with more and more animal power until the feeling grew within him. It was like a rising wave that affected every cell in his body, like some sort of pressure building, like he was getting closer and closer to the moment where the dam would break.

Then, he moaned.

His back arched. His unmistakably feminine voice let out the sweetest sound. Even his legs shook as he spurted pathetically out of his cage, soiling the edge of the mattress with his sissy sperm. It lasted longer than he expected, a sort of overwhelming feeling that permeated his entire being for several seconds, not so much ending as fading more and more with time until it had leveled off.

Then, he felt a warmth filling him from behind, gushing out and making wet sounds until the thrusting stopped.

"I knew you'd be one of my favorites" said the headmaster, grabbing Adam's plug and shoving it back inside. It trapped his seed inside Adam's hole and locked shut to keep it there.

"Sorry, sissy" giggled Ally, jumping on the bed in front of Adam as the headmaster laid a hard smack on his rear.

What... no... no, no, no this couldn't be-

"I can be pretty light on my feet when I want to be. Was worried you'd hear me but... they never do" chuckled the headmaster, patting the plug. "I have to admit, you have a long way to go. But even to a guy who has it all, popping a new sissy's cherry is a special-"

"You son of a bitch, you bastard, you fucking monster!"

SMACK

Adam sobbed as the headmaster struck him, his red handprint stinging on the student's already red face. "I'll let that go because losing their virginity makes anyone emotional but if you talk like that again, I'm taking you to the basement. And I won't need to trick you to do this down there" he promised before storming out of the room.

Ally watched him go and then undid Adam's bonds. He just laid there as she left, until the guards came and escorted him back to their dorm.