—
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.
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