Maid to Serve: Birthday Sissy Ch. 03

*Author's note: This is another short entry, but the next chapter will be coming up soon and will be nice and long!*

Matt woke up Friday morning to a shock: Britney, already dressed for work, lying between his legs and dangling the necklace above his cage. The key swung back and forth, its arc grazing the tip of the cage.

"Good morning little miss sunshine," she said sweetly.

"Hi," Matt said groggily.

"I thought that I'd give you an early birthday present, honey. Does that sound nice?" She tapped the key against the cage's lock.

"Oh, yeah. Yes, please. That would be wonderful," Matt said, suddenly sounding more awake.

He was long past the point where he thought staying chaste was necessary. First of all, he must have built up so much unreleased sexual energy, not to mention cum, that even the most earth-shattering orgasm now would surely not leave him unwilling to perform his maidly duties tomorrow. But even more than that, he just really wanted to cum. Who cares if he changed his mind and they had to cancel the whole dinner thing?

Britney smiled. She inserted the key and twisted it. The lock flung open. Matt was moaning already. Perfect, she thought.

"OK honey, let's try not to finish too quickly," Britney said as she removed the cage from his penis and the ring from around his balls.

"I'll try," Matt said, certain that he wouldn't last beyond two minutes. His erection was already three-quarters full, and a single delicate lick of his cock's now extra-sensitive head by Britney had him fully engorged. He moaned louder.

"Come on now, calm down. Let's chat while we go to keep you a little distracted," Britney said. Matt let his head fall back onto his pillow.

"Ugh, OK," he said.

"Well, I was thinking," Britney said as she wrapped her right hand weakly around Matt's cock. "Since we got you your little dress, your service and attitude have been exceptional."

Matt grunted a thank-you.

"And I was thinking of how we could ensure that you carry that level of performance over to the dinner tomorrow."

She started moving her hand up and down Matt's shaft slowly, still with a featherlight grip.

"I think the uniform really helps you get in the right headspace. So I had an idea."

For emphasis, she stopped stroking and let go entirely of the cock. Matt's eyes shot open.

"I am NOT wearing the maid's dress when Alexa is here," he said, sitting up onto his elbows to look at Britney.

"No, no, no, of course not," Britney said and immediately resumed the hand job. "I don't want Alexa to see you like that, either. Though I kind of think you secretly wish she did."

Matt tried to protest but instead just groaned and fell back onto the bed, eyes again closed in pleasure as Britney stroked his cock every few seconds.

"But I was thinking," she said, "the apron is not really very girly or anything. It's hardly even frilly. It's basically unisex. You could wear that."

Matt again opened his mouth to protest but Britney tightened her grip and sped up her stroking. He only let out a pleasured groan.

"Think about it. It would help you channel your inner sissy maid. And it would be so sexy. It would be a symbol that you're my feminized little house maid, right out there for her to see, except she won't actually know what it means."

Matt was already lost in the middle of the hand job -- it was the most sensual and pleasurable he had ever received, as if he had never been touched before. And with each stroke, he became hornier and his fantasies and desires more exaggerated. He pictured himself wearing the apron over his regular clothes as he carried a tray over to Britney and Alexa at the dining table. Then he imagined the girls watching him as he worked in the kitchen -- this time dressed only in his G-string and the apron.

Even as he let himself explore the pleasure of such imagined humiliation, he also became more and more eager to cum, and to cum immediately. How good that would feel. He was already so close.

Britney suddenly stopped mid-stroke, her hand still on Matt's shaft. "Well?" she asked.

Matt's mind raced for a moment. He might as well just agree, he thought. Wearing the apron would probably be fine. It wasn't too frilly, as Britney had said. And he could talk his way out of it later if he changed his mind once the orgasm had cleared his head.

"Sure, sure, keep going," Matt said hurriedly.

Britney smiled. "Perfect."

She continued to jack Matt's cock, which along with her hand was now coated in a thick layer of precum. With each stroke, her hand glided all the way from the base of the cock up to the tip of its head.

Her plan had worked flawlessly. Now for the final touch, which would ensure he maintained his eagerness for tomorrow's event.

She quickened the pace of her stroking. Soon, Matt's moaning changed, becoming more frequent. Britney knew what this meant: he was close, but not too close. She began stroking as fast as she could. With each downward thrust, the bottom of her hand bounced against the top of his balls. Now, Matt's moaning changed again, this time becoming higher pitched. It was almost time. After five more strokes, she felt Matt begin to writhe in a familiar fashion. Now! She let go of Matt's penis and grabbed each of his wrists with her hands, leveraging her bodyweight and position to keep Matt's arms pressed against the bed.

Matt let out a startled cry and reflexively tried to grab his cock but couldn't escape Britney's grip. He looked at her desperately as his penis twitched in the air.

"What?!" he shouted and tried again to free his hands but it was already too late. He let out a pained cry as a spurt of cum shot weakly out of his cock.

Britney beamed and leaned in closer to watch. Another squirt of cum came out, this time in more of a dribble. Then two more, covering his shaft and thighs.

"What was that?!" Matt demanded, his arms still restrained.

Britney looked at him innocently. "An early birthday gift," she said. "But we couldn't risk ruining tomorrow. This way, you get a release, but you're still motivated. Everybody wins."

"I don't," Matt said angrily. She was right--he could still feel his horniness raging--but this had been a genuine disappointment. "That wasn't a real orgasm."

"I control your orgasms," Britney said, and released Matt's hands. As she spoke, she slid her finger up Matt's still rock-hard shaft, collecting cum as she went.

This time, it was planned.

"I hold the key, and I decide the terms of when you orgasm. And one of the terms is that a good sissy maid always cleans up her messes." With that, she swiftly moved her hand toward Matt's face and shoved her cum-covered finger into his mouth. Matt wanted to resist but something in him felt compelled not to. After a few seconds, Britney withdrew her finger, wiping it clean against Matt's pursed lips as she did.

"Go put your cage back on."