Help Wanted Pt. 02

"Now, I have gagged you since this is your first punishment, but in the future I require my maids to thank me for each correction of behavior. Do you understand?" Mistress said sternly. Brianna nodded yes.

"Good. I think five should be sufficient." Mistress said.

Without warning, Brianna felt Mistress Anne's hand land firm and hard on her butt, making an audible crack when her hand hit the flesh. Brianna screamed into her gag on instinct.

"Bad girl, if you do that again I will add 5 more." Mistress said. Brianna braced herself and felt yet another smack, her bottom now stinging. This time she did not scream, and before she could catch a breath, another smack hit, then another, and finally the last. Brianna could feel the tears running down her face, and her bottom felt almost numb.

"You did well for your first spanking." Mistress said, removing the gag and placing the chair back against the wall. Mistress pulled back the curtain. Brianna was unable to move, still in shock.

"Very good, however we still have some things to discuss, will you please take a seat?" Mistress directed Brianna to the adjacent chair. Brianna tried her best to arrange her skirt while sitting down, while Mistress watched approvingly. As she sat, the pressure from her new bruise nearly made her yell out in pain. Mistress just smiled at her discomfort.

"Brianna I know that this has been a huge adjustment for you today, after experiencing your first punishment, how do you feel about your decision to take this job?" Mistress asked.

Brianna thought for a moment. "While this job is far from what I expected, I think I do like it and would like to stay." she nervously replied.

Mistress Anne smiled. "That's wonderful to hear. I am here to support all of my maids, while it's true that you are technically my employees, I do care about your wellbeing and delight in helping each and every one of you become whatever your heart desires." she said sweetly.

Mistress then pointed at Brianna's artificially enhanced chest. "For example, I have a doctor friend who can help you make those permanent, with either hormones or implants if necessary. But you must be the one to want that, not me." she said.

Brianna paused. "You mean you can help me become physically female?"

"Of course, surely you are aware that this is possible?" Mistress replied.

Brianna had of course heard of such treatments. But she had never considered this something she could realistically do.

"I think I might like that Mistress." Brianna meekly responded.

"Oh wonderful! I'll see what I can do." Mistress joyfully replied. "In the meantime, keep working on your etiquette and being the best maid you can be."

"Well Brianna, I think that is all. I will give you the rest of the day off, you may feel free to rest in either your room or the third floor common room. At night I will come up to unlock your clothes and help you dress for bed." Mistress said. "You may go."

Brianna stood up, struggling to stand thanks to her still-stinging bottom. She curtseyed and made her way out of the room. She made her way to the service stairs, struggling to walk. Each step made her satin panties slide across the her sensitive bruised butt. She finally made it up the stairs and collapsed on the couch. She put the TV on, drifting in and out of a nap. Her thoughts drifted into dreams as she contemplated her future in this daring new life. She never would have imagined that she would agree to anything like this, yet here she was, trapped in a sexy satin maid uniform, her genitals locked in a strange device that only a woman she barely knew had the key for. If she had any regret, it was most likely fear. But fear from what? There was no one left in her life to criticize her decision. She dozed off in the middle of a boring daytime sitcom contemplating her new position in life.

Hours must have past, because when she awoke dusk had arrived, and a familiar face was standing over her.

"Hi Brianna, have a nice nap?" said Allison, hands at her hips.

Brianna sat up, a bit startled from the intrusion. "Oh Allison, Mistress gave me the day off" she replied.

"I know, Mistress told me you might need a friend right now." Allison said. "I know, why don't you come to my room and we can talk?"

Without speaking, Brianna stood up and followed Allison to the end of the hall. Allison opened the door to her room, a much nicer suite than she was given. It was also not at all what she was expecting. Where her room was spartan, Allison's room was decorated very much like a teenage girl's room from a sitcom. The bed was a four poster canopy bed with elaborate purple curtains and sheets, the walls were also a matching shade of purple and she had many nice things, a larger TV than the one in the common room, and what Brianna recognized as a very nice gaming PC. The closet door was open, and Brianna could see dozens of satin maid outfits in many different colors, though most were still black.

"You must not have seen your closet but it looks like that too, we all have the same complement of clothes." Allison said. "Maids are pretty much only allowed to wear these satin uniforms while in the house, so we have different colors for different occasions." she said.

"It's kind of a perk of the job, how many other people get to wear these fantastic clothes all the time?" Allison added. She sat herself down on the bed and indicated for Brianna to follow. Brianna sat, her bottom feeling less bruised but still stinging when she sat.

"So Brianna, I know Mistress gave you your first punishment, are you feeling okay?" asked Allison.

"It's still sore, does this happen often?" Brianna asked.

"Oh it depends on the person. I haven't had a disciplinary punishment in ages." Allison said. She then smirked. "But if there are punishments you enjoy, then if you're very good you can ask Mistress to punish you with them as a reward."

Brianna winced, she couldn't imagine actually choosing to endure a spanking.

"Don't fret about it, but who knows? spend enough time here and you might awaken your inner pain slut" Allison said, giggling. She then playfully poked Brianna's fake silicone boob.

"Hey!' Brianna yelped.

"So Mistress also asked me about some treatments to make those, uh, permanent." Brianna nervously said.

"Oh? What did you tell her?" asked Allison.

"I said I think I would like to start those." Brianna replied.

Allison smiled. "Somehow that doesn't surprise me. I had them done myself." She said.

"So... yours are real?" Brianna asked, now staring at her new friend's tits.

"Yep, also my eyes are up here silly girl" Allison said playfully.

Brianna quickly averted her eyes. "Sorry." she nervously replied.

Allison reached out to hug her. "Hey, I was just playing around, I actually like when people look at them." She said. Allison then turned a bit. "If you unzip me you can get a closer look!"

Brianna paused, unsure how to respond. But then she remembered her own dress having rings and a padlock on the back, which Allison's seemed to lack.

"Wait, why isn't your dress locked?" Brianna asked.

"Oh, yeah, it's a perk I get for being a good girl on the regular. Mistress only lets girls she can trust go around without a lock." Allison said. "So, you want a peek or not?"

Brianna grabbed the zipper, slowly pulling it down. Allison then pulled off her dress and spread it neatly on the bed, revealing her purple pushup bra and the white petticoat around her waist. Her breasts did indeed look very real, they were barely held in by the bra and spilling out of the top. Allison reached behind her back and undid the clasp, letting her bra fall to the floor. There before Brianna sat the most perfect boobs she had ever seen.

"You can touch them if you want." Allison said coyly. Brianna reached out both hands, feeling the smooth skin and Allison's perfect nipples between her fingers. Allison moaned a bit, clearly enjoying Brianna's fondling.

"Oh yes Brianna, that's wonderful." Allison breathily exclaimed.

Brianna kept it up for a while, and paused. Allison snapped out of her euphoria.

"Why did you stop?" Allison asked, sounding disappointed.

Brianna had a curious expression. "I was wondering, do you, uh, still have your lower junk?" she asked.

Allison paused for a bit, stood up, and slid her petticoat down along with her matching purple panties. Before her stood a respectable sized dick. Or was it clit? Brianna wasn't entirely sure how she was supposed to describe it when not in it's plastic prison.

Allison stood there, as if trying to put herself on display.

"You can touch that if you want too." she said, making her desire clear. But Brianna was unsure. She had never touched another penis other than her own. Was this a step too far? But this was no ordinary experience, she had never been in the presence of someone quite like Allison. Allison had a nearly perfect feminine shape under all of those ruffles and petticoats, save for her apparently unrestrained dick. Why was it that she wanted so much to touch it? Without thinking, she stood up and began to run her hands over the shaft, Allison moaned louder than before. She pushed Brianna to her knees, and Brianna just stared at it. She had seen this scene before in porn, but she always imagined she was on the other side. But here she was, undeniably the "girl" in the scene, with her still perfectly done makeup, frilly black maid outfit, stockings, and heels, staring down a penis and contemplating what to do. Without thinking, Brianna licked the tip. She could taste the drops of Brianna's juices, it was better than she expected.

"You know, they say that us girls have the best tasting clits." Allison said, her voice wavering in ecstasy. Brianna had no experience to compare this with, but it was not unpleasant. She took another lick, and then took the tip into her mouth like a lollipop. This sensation was unlike anything she experienced, it was very warm but also smooth, and she could feel it still dripping onto her tongue. The taste made her want more. Brianna could feel her own clit swelling in its plastic tube, desperate for someone to do to her what she was doing for Allison. She grabbed the shaft with one hand, and began working it in and out of her mouth. She could feel it throbbing each time Allison's body shuddered in pleasure, each wave releasing more drops of that sweet nectar into her mouth. As she kept sucking up and down the shaft, she could feel Allison become more and more desperate for release, grabbing her head and trying to thrust into her mouth. Brianna would periodically stop to suck the tip, enjoying how each time made it twitch and throb.

"Oh shit - Brianna I think I'm about to cum!" Allison exclaimed, gripping Brianna's head harder. Brianna felt a vigorous throb and suddenly her mouth was overflowing with a warm, thick liquid. She held on, as Allison's body shook with waves of pleasure a little more came out each time, Brianna tried her best to swallow it. Allison's dick popped out of Brianna's mouth as Allison collapsed onto the floor into a pile of pillows in the corner. Brianna sat there in silence.

What had she done? The realization of of this came over her, she just sucked a dick! And yet... she liked it? Did this mean she was gay? But Allison was a girl. Was Brianna also a girl? The confusion paralyzed her, she was left simultaneously wanting to feel Allison's shaft inside of her mouth and more of that sweet cum while also repulsed by what she had just done, as well as the implications. She felt a simultaneous satisfaction and shame from what she just did. Meanwhile, Allison was working herself back to reality from her orgasm. She sat up and looked at her dumbstruck mentee still kneeling.

"Well congratulations Brianna, I assume that was your first?" Allison asked.

Brianna couldn't speak, she just nodded.

Allison laughed. "I guess you're officially a sissy maid now." she said.

Brianna finally spoke. "A what?"

"You know, the guys on the internet who dress up in maid costumes and suck off guys and girls." Allison cheerfully said.

Brianna just stared. Is this what she was now? The evidence was undeniable, she looked the part and just, er, did the part.

"I'm just kidding silly." Allison said, moving over to give Brianna a hug.

"You just did a brave thing, stepping outside of your boundaries. You should feel proud of yourself, not ashamed." Allison cooed.

"Did you enjoy it?" she asked?

"...yes" Brianna replied.

"Good." Allison said. "Don't worry about labelling yourself or trying to figure out how well you fit into other people's descriptions for what you might be. What matters is that you like you whatever that means."

"Thanks Allison, I think that actually helps." Brianna replied. She certainly did feel much more certain about herself.

"I must admit Brianna, you did a very good job. I haven't had much of a chance to orgasm since Mistress got me the hormones, they certainly do amplify the experience." Allison said.

"How so?" asked Brianna.

"Oh well it's hard to describe, but you know how the male orgasm is very immediate release focused?" said Allison. Brianna nodded.

"Well the female one is different, it's more like waves of pleasure moving over your body after a slow and steady buildup of heat. I wouldn't say one is necessarily better than the other, they're just different." said Allison.

Brianna wasn't even aware that this was possible, but she was curious to experience it for herself.

Allison stood up. She began to put her clothes back on.

"Brianna, you should make sure you didn't drip any thing on you and check your clothes, I think Mistress is coming soon to help you out." said Allison as she was hooking on her bra.

"That was fun, we should do it again some time." Allison said, smirking.

Brianna looked over her dress and apron, thankfully there were no spills. She smoothed everything over and as she stood up to leave, Allison gave her a quick kiss on the lips.

"Goodnight sweetie, see you tomorrow!" she whispered. Brianna made her way back to her room.

Soon after she returned to her room, she heard a knock on the door. Brianna opened the door.

"Hello Brianna, I'm here to help you out." Mistress said.

Brianna stepped aside and Mistress Anne entered the room. She pulled out a key and undid all of the locks on the clothes.

"Normally I do not actually put the locks on every day, I let the maids dress themselves. I do this for first timers and as a punishment to teach you that I am in control of your wardrobe, do you understand?" Mistress asked.

Brianna meekly replied "Yess Mistress."

"Good. Now, take off your dress and put it in the closet." Mistress ordered.

Brianna untied the apron and slid off the dress. She grabbed a satin wrapped hanger out of the closet and carefully put the dress and the apron on the hanger. Mistress then helped her out the corset, bra, and breast forms. She was then shown the dresser where a large array of nighties in different colors sat neatly folded.. Mistress picked out a pink one and had Brianna put it on. She slid it over her head, shivering a bit as she felt the satin fabric slide over her body.

Mistress smiled. "I'm glad you like the clothes we have provided. Once you start receiving paychecks, I can help you get nice things for your room. We give the girls a bit of freedom in their own rooms as long as you keep things tidy." she said.

Brianna sat on the bed, and Mistress moved toward the door,

"Good night sweetie, I'm very happy you've joined us!" Mistress said as she exited the room. Brianna sat in silence for a bit, and then got into the bed, slowly drifting off to sleep.