High School Chastity Ch. 02

It had been three days since Adrian had come home with her key. Three days since becoming Adrian's charge and three days since their relationship had shifted forever. They were no longer equals - Adrian had emphasized that clearly. She was to be teased, denied and occasionally rewarded and Adrian was the one who decided when to do what.

Jess shifted around on the couch, irritated at herself. She should have known that Adrian would do that - the tutors told him he was a natural at Keyholding! She just hadn't thought that would extend to their relationship.

She idly sneaked her hand through her t-shirt, rubbing her nipples through her bra. It was a habit that most girls (or boys, for that matter) developed after being locked for more than a few weeks. As she continued the circling motions and felt her nipples grow hard, she morosely remembered that the same people stopped the habit after truly long periods because it only made them hornier at that point.

It seemed that she was becoming one of them now. Even her nipples were now enough stimulation for her breath to quicken and hand to start wandering around her jeans.

As always, her hand came in contact with her cold steel belt instead of the soft flesh underneath. She sighed in defeat. She was locked in her belt for the next year at the minimum. She decided to do her best at earning as many climaxes as possible.

---

"You free today evening?" Adrian's text was perfunctory and gave absolutely no hint to his intentions. While Jess was pissed at him for being such a stickler to the keyholder code, she couldn't help but respond; it's not like she could orgasm without the key in his hands.

"Yeah."

"See you soon."

---

Jess opened the door to a casually dressed Adrian, holding a black bag. He strode in without comment, and only said one word: "Upstairs." She hurried behind him, keenly aware of what was about to happen.

She came into her room to find Adrian tying ropes around the legs of her bed.

That was... not what she thought was about to happen. Adrian looked at her, and then nodded to the bed as if it was obvious. Jess hesitantly laid down, while he continued to bustle around the bed tightening the ropes.

"Do you want to strip? I'll rub your nipples if you want." Adrian's voice was gentle, as if he was a doctor talking to a patient.

She silently undid her shirt and bra, and wiggled out of her jeans. Tossing them in a pile in the corner, she lay facing the ceiling with her arms and legs spreadeagled. Adrian gently took each limb and tied it with the bedposts.

"Try pulling your hand hard." She did so. The only thing it accomplished was hurting her wrists. Her hair caused her neck to itch, but all she could do was turn her head slightly.

Adrian knelt beside her head, and his face suddenly intruded her vision.

"I'm going to put a pillow beneath your head so you can watch. Would you like that?"

She nodded once. She was rather pleased with how gently he was treating her.

Her vision tilted down, enough that she could look at her belt from between her cleavage. Adrian pulled out a key from somewhere and waved it over her belt, and the lock immediately disengaged.

After an year, Jess felt fresh air down there. It felt cold. She could see the faint fuzz of pubic hair that had spread after the last time she'd gotten some depilatory cream down there.

Adrian shifted closer to her feet, bent down, and blew. Blew gently on her vulva. It was cold, yet ticklish.

She could feel her vulva pump with blood and enlarge, become aroused. She could almost see it shimmering in the low light, so close yet so far away. She felt a pressure on her arm.

Adrian was holding it down, to prevent it from straining against the ropes. Her hand had acted without conscious thought and had been struggling with the ropes for a while now. She blinked.

"Relax. You're going to get a release," he soothed her.

Having done so, he turned back and carefully brought his finger near her abdomen. He slowly traced his way down to her stomach, then nether regions. He swirled the skin just above her quivering hood, and the most Jess could do was arch her back at the sensation.

She screamed in frustration. First he blew on it, and now he was teasing her? She wanted an orgasm, dammit! She was so horny! She wanted to feel the deep pleasure spreading from inside after a long session with a dildo, or the fuzzy warmth from playing with her clit. "Fuck you, I want to cum!" She yelled out the last part.

Adrian's hands blurred, and before she could react, he was holding her mouth shut. He smiled.

"I know this is difficult for you. But remember, a lot of people go through what you're going. If you try to enjoy it, you just might! You're lucky to have your boyfriend as your keyholder - I'll kiss you, pet you, and touch you in all the ways you need to make your orgasms satisfying. Not many keyholders do that!"

She calmed a little bit, and shook her head in acceptance. His hand was still keeping her jaw shut.

"I'm going to put in a gag to stop you from screaming again. Ok?"

Jess paused, but Adrian kept looking intently at her, still holding her mouth firmly shut. It was clear that he wasn't going to proceed without inserting a gag first.

She meekly nodded.

He turned out of her limited vision. His hand started to relax on her jaw, but she made no move to speak. He then gently pulled her mouth open, and then gently inserted a large ball gag behind her teeth. The ball itself had holes all over, so she didn't have any difficult breathing, but it was large enough that she couldn't help but drooling immediately.

Soon enough, drool made way to her collarbone and breasts. She felt utterly humiliated. Naked, tied down, and now drool spreading over her chin, all while her keyholder merely stroked her hair.

Once Adrian was satisfied with her gag, his hand gently went to her pussy. He gently massaged it, with a steady pace that drove her mad. She was so wet that she had begun leaking! As if finally noticing the fact, Adrian brought forth a vibrator and held it against her lips. She struggled against it the best she could, quickly reaching an orgasm. Finally!

Even her moans was mangled by the gag. At this point, her chin felt cold. She shook in her restraints and quickly climbed to her climax. At this point, nothing could stop her. She came within a minute of the vibrator touching her, and saw red as fireworks exploded inside her head. She relaxed slightly in her bondage, turning to Adrian. He leaned in, and kissed the ball that blocked her from speaking.

"You enjoyed it?"

She nodded.

"Good girl."

That praise made Jess feel warm inside. She was been a good girl. She strained her neck to get closer to him and tried to beg for a kiss with her eyes. It must've been enough, since Adrian once again leaned in and kissed her lips around the gag.

She was panting slightly now, after the exertion of an orgasm in so long. Adrian chuckled.

"Let's get you untied now."

And soon enough, she was once again belted and lying with her head in Adrian's lap. She was still naked, and had gotten Adrian to remove his shirt. He stroked her hair and she looked up at him affectionately.

It was somewhat alarming how quickly she had gotten accustomed to Adrian being her keyholder instead of boyfriend. He was stern and strict during the times she whined, but otherwise treated her affectionately and as an equal. Really, the only thing that had changed was in the bedroom.

Speaking of bedroom things, Adrian's erection hadn't gone unnoticed by her. Still naked but belted, she rose up and playfully tackled him down. She may have been belted, but it didn't mean that he had to remain unfulfilled. She quickly tore off his underwear and humped his crotch. Her pussy was once again wet, but she ignored the sensation in favor of watching his face. He bit his lip. He wanted her.

She mashed her boobs into his chest and kissed him deeply. His hands automatically made their way to her bottom where he tightly groped her butt. She'd always liked his groping. It made her feel wanted.

She quickly scrabbled down to his cock and hungrily enveloped it with her mouth. Her pussy felt like it too, was throbbing beneath the belt, but she was learning to ignore it. She instead worked her tongue around the head the way he liked it, and was pleased to feel his cock harden even more.

Adrian had put his hands on top of her head, and with every bob felt his penis enveloped in a warm, wet and stimulating environment. Jess's hair were messy and stuck to her back, but her eagerness to please him made her look all the more beautiful in his eyes.

After minutes of furious pumping, Adrian shot his load in her mouth. Surprisingly, she didn't pull away, and instead, with her mouth still holding his dick, looked into his eyes, and swallowed.

She finally pulled away and smiled. Before Adrian could say anything, she said, "I just wanted to do it. Maybe it's because I'm so horny, but the idea didn't sound gross at all!"

Adrian was impressed. She was adapting well to supervised chastity. Jess sucked him off again after he got hard enough, and soon he was giving her a farewell kiss for the day.

---

It was bitterly cold on the subway today. Adrian felt underdressed in his casual T-shirt and jeans, and shivered in the cold. He was no longer a charge of the state. He was a keyholder himself, with two charges.

Indeed, he had gotten the call just that morning. He was going to be assigned another charge due to his exceptional performance in the SEKS exam. He was somewhat taken aback by the suddenness of it all; he hadn't even had the time to break the news to Jess yet, and the Bureau wanted him to take on another charge.

He closed his eyes. It was time to channel the dominant he had spent years building inside him, practicing his tone and posture in the SEKS Scenarios, and show the Bureau he could take on this challenge.

His penis had almost recovered from its extended chastity and was nearly at full size. He was still unused to having to adjust his jeans to hide erections that he hadn't had for so long, but he managed.

---

The Bureau building was hard to miss, what with the giant logo of a key across a lock in the front. He walked in briskly, feeling equal amounts of deja-vu and trepidation.

He walked to his appointed booth, to see the clerk engaged in conversation with a tall woman. It was clear that she was close to his and Jess's age. She had pale skin with straight black hair, and strong Korean or Japanese features.

He simply took his position behind her, hoping that he wouldn't have to wait too long in line. Just as he was moving, however, the woman noticed him and immediately moved back. Her voice was high-pitched and airy.

"Oh, you can go ahead! I'm waiting for someone."

He nodded in understanding, and moved forward. He handed his documents to the clerk, who glanced at them and immediately called, "Hey, lady! Your keyholder's here."

The woman who'd retreated immediately came to the booth. "Oh, so you're Adrian? I'll be in your care!"

Adrian was amazed at his good fortune. This woman was just as hot as Jess. She also seemed rather good-natured by her voice and mannerisms. It seemed he wouldn't have to work very hard as a keyholder after all.

Looking closer, he vaguely recognized her. He'd seen her around his neighborhood a few times. He confirmed by looking down at her papers. Yup.

The clerk started speaking.

"Now that the both of you are here, I need to let Adrian know about a few things. First, you have been given the rare honor of having more that one charge. Don't let this opportunity go to waste and you can create a very good career for yourself. Your second charge's name is Sophie, and she has had a troubled chastity record, which you will be in-charge of very shortly."

Sophie visibly cringed on hearing that. Adrian was surprised as well. He hadn't pegged her for a troublemaker.

"She was most recently caught trying to sneak an orgasm six months ago, and has been under extra surveillance since."

The clerk handed him Sophie's key. Holding it, it seemed different then Jess's. Perhaps her belt was a different model? Odd.

Just as Adrian thought about leaving, Sophie spoke timidly, "Are you free for the afternoon? I'd like to get to know you better." Adrian chuckled.

"That was quick. Since we're neighbors, why don't we have lunch at old Frank's?"

She blushed. She really was cute. Adrian could relate to wanting an early release, and he was planning on giving one to both of his charges. An orgasm early on could help motivate charges to better themselves by reminding them what they were missing out on.

"I presume you know that you're my second charge?"

Sophie nodded eagerly. "I'm perfectly fine with that. Let's go."

---

He'd gotten to know Sophie better over their date. She was ditzy, cheerful, and a fun person to be around. She must have felt comfortable enough with him to invite him to her apartment after their first meeting. Of course, she also could have just been extremely desperate for a proper release.

As soon as Adrian had entered, Sophie began removing her dress. It surprised him a bit - most people were desperate, but not usually so desperate that they dropped all pretense. As Sophie's dress came off, Adrian did not resist ogling at her breasts. They were not absurdly large, and they were just the right size for her frame and bounced slightly. As she undid her bra, her dark nipples spilled out, slowly hardening. She pulled down her panties, revealing an unexpected bulge.

As Adrian looked at the testicles beneath the flat exterior of the cage, Sophie blushed.

"Ah, by your face you hadn't realized I was trans?"

Adrian merely shook his head, continuing to look at the special flat cage that was only awarded to charges on request or bad behavior.

Noticing his gaze, Sophie shyly tucked her arms beneath her back and explained.

"The cage is flat to encourage shrinkage. I didn't want to have a clit larger than necessary."

At this point, Adrian had recovered from his shock. His dick too had quickly sprouted an erection from Sophie stripping down in front of him, but his mind had switched tracks to recalling the treatment of trans charges.

Sophie seemed to be taken aback by his change of demeanor, but took a seat on the sofa, her breasts bouncing from the abrupt motion.

Adrian quickly tied her arms behind her back, then opened her flat cage with a wave of his key. He gently lifted her testicles outside the ring, and looked at her rather small flaccid penis.

Sophie shook her head. "I don't think it gets hard anymore."

He gently touched her penis with his hand, watching her reactions. She cringed a bit at the stimulation, but didn't look like she was uncomfortable.

"Do you want a vibrator?" Sophie bit her lip, and nodded. His erection intensified. He had cute girl tied up on her couch, with her penis in his hand. It was a feeling of power very similar to what he'd experienced with Jess, yet slightly different.

He brought out a condom and pulled it over her one-and-a-half inch penis. It looked so cute! The cage seemed to have shrunk it significantly from an average size.

He struggled for it to hold in place, but once he was done, he gently brought the vibrator to her balls. They were small and hairless, like his before puberty.

"You started taking hormones from an early age?"

Sophie's face betrayed her extreme arousal, yet her penis stayed flaccid. It had begun to leak some precum, though.

Her voice had somehow grown higher in pitch.

"Yes, master."

The "master" surprised Adrian. It was an address that some keyholders did use, but since Adrian was Sophie's first keyholder, he was pretty sure she'd picked it up from erotica. Nonetheless, it turned him on, so he didn't comment.

Her penis continued to leak precum into the condom. He moved from the base to the tip of penis, and Sophie let out a tiny squeal. Sweat had begun to bead on her forehead, and her nipples stood out from her breasts. Still, she made no move to shift from her position in Adrian's lap.

Her arms were now straining against the ropes, but Adrian didn't mind. It was only natural.

"Master..." She was panting now. "May I kiss you?"

In response, Adrian lowered his head to her face. She attacked him with a passion, wriggling in his lap for the best angle, all while bouncing back-and-forth to increase the stimulation to her nether region. Sophie tried humping the vibrator, but she didn't find much success in that. All of the bouncing had made Adrian's erection very pronounced, and Sophie could feel it poking her in the back.

Sophie was ridiculously turned on. This fine hunk was her keyholder, and she was currently tied up in his lap with a vibrator on her clit. Her clit too had seemed to have finally broken, an event that caused her no small amount of relief. She was kissing him passionately and feeling sexy and feminine.

She pulled away from his face, panting from the sensations on her clit. She wasn't thinking rationally anymore. And besides, even though she'd met him today, he was her keyholder; she'd be seeing a lot of him over the year.

"Master... you're horny too. Why don't I help you out?"

Sophie cringed as Adrian suddenly removed the vibrator from her penis. She turned around to see him looking interested.

"What exactly do you have in mind?"

She blushed. She had masturbated a lot with dildos, and in fact the mark on her chastity record was from the time she'd been caught orgasming with a dildo five months ago. But she'd never had a penis in there.

Burying her face in his strong arms, she whispered, "My ass. Please. It's yours."

Adrian smiled. Sophie really was a cutie. He nibbled on her ear, and then whispered, "Turn around."

After putting on his own condom, he turned her bound form on his lap and gently inserted his penis into her ass. Her clit flopped uselessly, but both he and Sophie paid it no mind. Her hands were still tied behind her back, so she just wriggled about as he inserted himself.

Finally, Sophie gently lowered herself on his dick and gasped at the sensation. It had been some time. Her ass was loosening up and soon enough she was bouncing on his cock. Her modest boobs bounced around, and she smiled at him. He was such a nice keyholder to grant her this wish!

Adrian just held her, occasionally licking her neck and nipples. Sophie had thankfully trained herself to cum through anal stimulation out of dislike for her penis, so she was satisfied with this position.

His penis filled her like any other dildo, but it was warm. While that may have sounded minor, Sophie loved the new sensation. Her hole was stuffed and providing her pleasure while her finally broken clit just bounced around, leaking into the attached condom. Adrian pounded her with enthusiasm and held her gently. While she wished she could hold him too, having her hands tied behind her back and being used like this was fine too. He dictated the pace, and Sophie merely followed it.

Finally, she grew close to orgasming. Adrian had held on for a really long time, wanting to ensure his charge got to experience one good orgasm before he started limiting them for her training. Her penis dribbled out ejaculate into its loose condom, and he finally let himself go as well. His cock tightened and Sophie let out a moan. She collapsed on top of him as his now soft penis slid out of her ass. Her face was red from the thorough fucking she'd just received and she smiled at him.

Adrian smiled back. It truly had been some nice sex. His smile dimmed a bit as he realized he'd have to introduce Sophie to Jess soon. Ah well.

He gently laid Sophie on the sofa and smiled at her. The trans Asian woman smiled back at him. He removed the condom, washed her tiny penis, and then put it back in the flat cage. It fit perfectly.